Heterocyclic Building Block-benzofuran

With the rapid development and complex challenges of chemical substances, new drug synthesis pathways are usually the most effective.28033-47-8,5-Chlorobenzofuran-2(3H)-one,as a common compound, the synthetic route is as follows.

A. a solution of 47.6 parts by weight of 2-hydroxy-5-chlorophenylacetic acid lactone in 560 parts by volume of glacial acetic acid is treated with 59.2 parts by weight of sodium nitrite at 10C to 20C. The reaction mixture is stirred for 4 hours at 15to 20C and poured into 1700 parts by volume of ice water. The reaction product is collected by filtration, washed with water and dried in vacuo over potassium hydroxide to yield 51.5 parts by weight of 5-chlorocoumaranedione-3-monoxime, m.p. 192C (dec)., 28033-47-8

The synthetic route of 28033-47-8 has been constantly updated, and we look forward to future research findings.

Reference£º
Patent; Bayer Aktiengesellschaft; US3993665; (1976); A;,
Benzofuran – Wikipedia
Benzofuran | C8H6O – PubChem

496-16-2, 2,3-Dihydrobenzo[b]furan is a benzofuran compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

Preparation of 1-(2,3-dihydrobenzofuran-5-yl)ethanone Into a 500 mL 3-necked round-bottom flask, was placed a solution of acetyl chloride (62 g) in dry dichloromethane (400 mL). To this was added aluminum(III) chloride (55.6 g, 1.00 equiv). The mixture was allowed to react, with stirring, for 30 min at -10 C. (solution A). Into another 2000 nm 3-necked round-bottom flask, was placed a solution of 2,3-dihydrobenzofuran (50 g, 0.42 mmol, 1.00 equiv) in dry dichloromethane (500 mL) at -10 C. The solution A was added to the above via a cannula, and was stirred for 30 min at 0 C. The mixture was poured into ice/HCl (5:1 v/v, 1 L). The resulting solution was allowed to react, with stirring, for an additional 2 h while the temperature was maintained at room temperature. The resulting solution was extracted three times with 500 mL of CH2Cl2 and dried over Na2SO4 and concentrated by evaporation under vacuum using a rotary evaporator. The residue was purified by eluding through a column with a 1:100 EtOAc/PE solvent system. This resulted in 67 g (94%) of 1-(2,3-dihydrobenzofuran-5-yl)ethanone as a yellow solid., 496-16-2

The synthetic route of 496-16-2 has been constantly updated, and we look forward to future research findings.

Reference£º
Patent; MEMORY PHARMACEUTICALS CORPORATION; US2008/318941; (2008); A1;,
Benzofuran – Wikipedia
Benzofuran | C8H6O – PubChem

69999-16-2,69999-16-2, 2,3-Dihydrobenzofuranyl-5-acetic acid is a benzofuran compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

Step 3. 2-(2, 3~dihydro-l-benzofuran-5-ylmethyl)-N,N-diethyl-l-(piperidin-4-ylmethyl)-lH- benzimidazole-5-carboxamide [0201] To a mixture of tert-butyl 4-[({2-amino-4-[(diethylamino)carbonyl]phenyl}amino)methyl]piperidine-l -carboxylate (Step 2 of Example 18, 0.047g, 0.12 mmol, 1 equiv), 2,3-dihydro-l-benzofuran-5-ylacetic acid (0.023g, 0.13 mmol, 1.1 equiv) and DMF (5 mL) were added DIPEA (24 muL, 0.14 mmol, 1.2 equiv) and HATU (0.049 g, 0.13 mmol, 1.1 equiv). The mixture was stirred at room temperature for 3 hours. Complete consumption of the starting material was confirmed by LC-MS. DMF was removed under reduced pressure. Dichloromethane was added to the resulting residue. The organic layer was washed once with a saturated aqueous NaHCOs solution, once with brine and dried over anhydrous Na2SO4. Dichloromethane was removed under reduce pressure. The resulting residue was dissolved in dichloroethane (3 mL) and a few drops of concentrated HCl were added. The mixture was stirred at 80 C for 2 hours. Complete consumption of the starting material was confirmed by LC-MS. Dichloromethane was added. The organic layer was washed once with a 2M aqueous NaOH solution, once with brine and dried over anhydrous Na2SO4. Dichloromethane was removed under reduced pressure. The resulting residue was purified by reversed-phase HPLC (2 times) and lyophilized to afford 2-(2,3-dihydro-l-benzofuran-5- ylmemyl)-N,N-diemyl-l-(piperidin-4-ymiemyl)-lH-benzimidazole-5-carboxamide (0.007 mg) in 9% yield. 1H NMR (400 MHz, METHANOL-D4) delta ppm 1.08 – 1.18 (m, 3 H) 1.20 – 1.31 (m, 3 H) 1.45 – 1.59 (m, 2 H) 1.74 – 1.83 (m, 2 H) 2.02 -2.16 (m, 1 H) 2.74 – 2.85 (m, 2 H) 3.17 (t, J=8.69 Hz, 2 H) 3.33 – 3.40 (m, 2 H) 3.51 – 3.63 (m, 2 H) 4.28 (d, .7=7.42 Hz, 2 H) 4.42 (s, 2 H) 4.53 (t, J=8.79 Hz, 2 H) 6.74 (d, J-8.20 Hz, 1 H) 7.03 – 7.08 (m, 1 H) 7.15 – 7.19 (m, 1 H) 7.44 (dd, /=8.40, 1.17 Hz, 1 H) 7.68 (s, 1 H) 7.77 (d, J=8.59 Hz, 1 H); MS (ESI) m/z 447.0 (M+H)+; Anal. Calcd (%) for C27H34N4O2 + 2.1 TFA + 1.5 H2O: C, 52.55; H, 5.53; N, 7.86. Found: C, 52.48; H, 5.48; N 7.96.

As the paragraph descriping shows that 69999-16-2 is playing an increasingly important role.

Reference£º
Patent; ASTRAZENECA AB; WO2007/91950; (2007); A1;,
Benzofuran – Wikipedia
Benzofuran | C8H6O – PubChem

35700-40-4, 2,3-Dihydrobenzofuran-7-carboxylic acid is a benzofuran compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

c. Preparation of 5-nitro-2,3-dihydrobenzo[b]furan-7-carboxylic acid (15k) Method A: To an ice-cooled solution of 2,3-dihydrobenzo[b]furan-7-carboxylic acid (15a) (0.33 g, 2.0 mmol) in 3 ml of TFA there was added dropwise 0.6 ml of HNO3. At the end of 1 hour, the cooling bath was removed. After an additional 3 hours of stirring, the mixture was poured into ice-water. The precipitate was collected on a filter to give 0.22 g (52.6%) of crude 15k. This was recrystallized from ethyl acetate to provide 88 mg of acid 15k (21.4%), mp 249-251.5 C.

35700-40-4, 35700-40-4 2,3-Dihydrobenzofuran-7-carboxylic acid 2795014, abenzofuran compound, is more and more widely used in various fields.

Reference£º
Patent; Erbamont, Inc.; US4888353; (1989); A;,
Benzofuran – Wikipedia
Benzofuran | C8H6O – PubChem

With the rapid development and complex challenges of chemical substances, new drug synthesis pathways are usually the most effective.77095-51-3,Benzofuran-6-carboxylic acid,as a common compound, the synthetic route is as follows.

77095-51-3, A. 2-(4-Bromobutyl)benzofuran-6-carboxylic acid n-Butyllithium solution (2.29 M in hexane, 44 ml., 0.1 mole) is added to a solution of diisopropylamine (10.1 g., 0.1 mole) in tetrahydrofuran (150 ml.) and hexamethylphosphoramide (15 ml.). The resulting solution is treated with benzofuran-6-carboxylic acid (8.1 g., 0.05 mole) and then with 1,4-dibromobutane (10.8 g., 0.05 mole) at 0 C. The mixture is stirred at 0 C. for 6 hours. It is then quenched with water, acidified with hydrochloric acid and extracted with ethyl acetate. Evaporation of the solvent gives 2-(4-bromobutyl)benzofuran-6-carboxylic acid.

77095-51-3 Benzofuran-6-carboxylic acid 17867234, abenzofuran compound, is more and more widely used in various fields.

Reference£º
Patent; Merck & Co., Inc.; US4238487; (1980); A;,
Benzofuran – Wikipedia
Benzofuran | C8H6O – PubChem

4265-25-2, 2-Methylbenzofuran is a benzofuran compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated,4265-25-2

PREPARATION EXAMPLE 130 Tin tetrachloride (1.15 ml) was added to a solution of 6-bromohexanoyl chloride (2 g) and 2-methylbenzo[b]furan (1.24 g) in carbon disulfide (30 ml) under ice-cooling, the mixture was stirred at room temperature for 3 hr. Ice water and conc. hydrochloric acid were added to the reaction mixture, and the mixture was extracted with ethyl acetate. The organic layer was washed with water and brine, dried and the solvent was evaporated under reduced pressure. The obtained residue was purified by silica gel column chromatography to give 2.2 g of 6-bromo-1-(2-methyl-3-benzo[b]furyl)-1-hexanone. 1 H-NMR (CDCl3,ppm) delta: 1.52-1.63(2 H,m), 1.76-2.04(4 H,m), 2.78(3 H,s), 2.97(2 H,t,J=7.3 Hz), 3.44(2 H,t,J=6.6 Hz), 7.29-7.36(2 H,m), 7.42-7.47(1 H,m), 7.88-7.92(1 H,m)

As the paragraph descriping shows that 4265-25-2 is playing an increasingly important role.

Reference£º
Patent; Yoshitomi Pharmaceutical Industries, Ltd.; US5864039; (1999); A;,
Benzofuran – Wikipedia
Benzofuran | C8H6O – PubChem

82104-74-3, 1-Oxo-1,3-dihydroisobenzofuran-5-carbonitrile is a benzofuran compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

82104-74-3, (a) Synthesis To A suspension of 20 g of 5-CYANOPHTHALIDE in 150 ml of tetrahydrofuran, under nitrogen FLOW, AT 25¡ãC, 422.6 g of the 20percent solution of 4-fluorophenylmagnesium bromide obtained in PREPARATION I are added and a rise in temperature of the mixture to about 35¡ãC is observed. The mixture is kept under stirring until, by a HPLC control [COLUMN: DEVELOSIL C18 4.6 x 250 mm, 5 P ; DETECTOR: UV 240 nm; FLOW : 1.5 ML/MIN ; GRADIENT : A: aq. NH4H2PO4 + H3PO4-PH = 2.85/B : CH3CN/H2O = 9/1 (v/v) ], the disappearance of 5-cyanophthalide is observed. When the reaction is over, 200 ml of a 15percent aqueous solution of ammonium chloride are added, maintaining the temperature not higher than 30¡ãC, then the phases are separated and the organic one is concentrated under vacuum to obtain 52 g of a yellow oil, the raw 3-HYDROXYMETHYL-4- [BIS- (4- fluorophenyl) hydroxymethyl] benzonitrile, with a purity of 92.12percent. (b) Purification In a 250-ML FLASK, 20 g of raw 3-hydroxymethyl-4- [bis (4- fluorophenyl) hydroxymethyl] benzonitrile obtained in the preceding synthesis and 100 ml of ethyl acetate are charged. The mixture is stirred until a solution is obtained, wherein 30 ml of silica gel 60 are added, then the solvent is evaporated under vacuum until a dry powder is obtained. Separately, a 5-cm diameter column is prepared with 300 ml of silica gel 60 (particles 0 0. 063-0. 200 mm) for GRAVIMETRIC column, using A mixture heane/ethyl acetate 9/1 (V/V) as eluent. The product previously adsorbed on silica gel 60 is charged into the column prepared as described and is eluted with the mixture itself. The fractions containing the product are collected and concentrated under vacuum at 50’C with ROTAVAPORX (the solution is getting foaming, so that during the concentration must be taken the due precautions). The oily residue obtained is TREATED WITH 100 MI dichloromethane and the solution is concentrated to give 11. 6 g of 3- hydroxymethyl-4- [bis(4-fluorophenyl)hydroxymethyl]benzonitrile as white crystals with M. P. = 66. 4. 72. 3¡ãC AND PURITY (HPLC) = 97. 35percent. H-NMR and C-NMR PRODUCT DATA ARE INDICATED in Figure 1.

As the paragraph descriping shows that 82104-74-3 is playing an increasingly important role.

Reference£º
Patent; ADORKEM TECHNOLOGY SPA; WO2004/80988; (2004); A1;,
Benzofuran – Wikipedia
Benzofuran | C8H6O – PubChem

10242-12-3, 5-Nitrobenzofuran-2-carboxylic acid is a benzofuran compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

The achiral 2-(4-benzyloxy-2-nitrophenyl)ethyl chloride compound (0.500 g, 1.71 mmol) was dissolved in freezer-chilled THF (30 mL) and PtO2 (0.150 g) was added. The reaction was stirred while degassing under vacuum, followed by exposure to hydrogen gas. The degas/hydrogen exposure cycle was repeated 3 times, at which point the reaction was allowed to continue stirring under hydrogen at 50 psi at room temperature for one hour. The amine solution was filtered over Celite, and concentrated under reduced pressure. It was then coevaporated three times with dry CH2Cl2 (5 mL). A tan oil resulted and was placed under high vacuum, covered with foil for 30 minutes. Then, 5-nitrobenzofuran-2-carboxylic acid (0.394 g, 1.90 mmol) and PyBOP (0.999 g, 1.92 mmol) were suspended in dry CH2Cl2 (220 mL). The amine was then dissolved in dry CH2Cl2 (30 mL) and added to the suspension via a syringe through a septum. The reaction was allowed to stir for 10 minutes, at which point dry N,N-Diisopropylethylamine (0.75 mL, 4.29 mmol) was added to the suspension. The solution turned clear yellow. It was covered with foil and the solution was stirred under nitrogen, at room temperature for two days. The solution was vacuum filtered and the filtrate was washed with water (1¡Á75 mL), 10% HCl (1¡Á75 mL), saturated Sodium bicarbonate (1¡Á75 mL), and brine (1¡Á75 mL). The organic layer was dried over sodium sulfate, vacuum filtered, and concentrated under reduced pressure to yield a yellow solid. The residue was purified on a silica gel column using a 5-20% EtOAc/hexane solvent system to give the desired product 2-(4-benzyloxy-2-(5-nitrobenzofuran-2-carboxamido)phenyl)ethyl chloride as a yellow solid (0.173 g, 22% yield). Rf=0.22 (20% EtOAc/hexane) M.p. 109-113 C. IR (neat) 3370, 3088, 3032, 2945, 2858, 1690, 1531, 1337, 1270, 1168, 1101, 1025, 753, 610 1H-NMR (500 MHz, CDCl3) 8.67 (d, 2.0, 1H), 8.64 (s br, 1H), 8.39 (dd, 2.0, 9.0, 1H), 7.73 (s, 1H), 7.70 (d, 9.0, 1H), 7.65 (d, 2.5, 1H), 7.45 (d, 8.0, 2H), 7.40 (t, 8.0, 2H), 7.36 (t, 8.0, 1H), 7.19 (d, 8.5, 1H), 6.89 (dd, 2.5, 8.5, 1H), 5.10 (s, 2H), 3.83 (t, 6.5, 2H), 3.14 (t, 6.5, 2H). FAB-MS (NBA) 451 (M+H+, 11). Accurate mass for C24H19N2O5Cl+H: calcd. 451.1060; obs. 451.1050., 10242-12-3

The synthetic route of 10242-12-3 has been constantly updated, and we look forward to future research findings.

Reference£º
Patent; Taiho Pharmaceutical Co. Ltd.; US6660742; (2003); B2;,
Benzofuran – Wikipedia
Benzofuran | C8H6O – PubChem

With the rapid development and complex challenges of chemical substances, new drug synthesis pathways are usually the most effective.23145-07-5,5-Bromobenzofuran,as a common compound, the synthetic route is as follows.

250 mL reaction flask 5-bromobenzofuran (21 g, 0.1 mol) P-aminophenylboronic acid pinacol ester (21.9 g, 0.1 mol) PdCl2 (dppf) (4 g, 0.005 mol) Potassium carbonate (27.2 g, 0.2 mol), 100 mL of DMF, and the mixture was purged with nitrogen three times. The reaction was heated to 100 ¡ã C, And stirred overnight. To the reaction solution was added saturated brine (300 mL)Extracted with ethyl acetate (100 mL x 2), combined with the organic phase,Dried, filtered, and concentrated in filtrate. Purified by column chromatography, Compound 9-1 was obtained as a white solid product(19.8 g, yield: 89percent, purity 98.2percent),used directly in the next step., 23145-07-5

As the paragraph descriping shows that 23145-07-5 is playing an increasingly important role.

Reference£º
Patent; Shanghai Haoyuan Pharmaceutical Co., Ltd.; Douchuang (Shanghai) Pharmaceutical Technology Co., Ltd.; Li Shuoliang; Feng Qifei; Wang Xiaolei; Li Gangqin; Wang Lei; Gao Qiang; Zheng Baofu; (14 pag.)CN104876917; (2017); B;,
Benzofuran – Wikipedia
Benzofuran | C8H6O – PubChem

37418-88-5, 4-Hydroxyisobenzofuran-1,3-dione is a benzofuran compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

4-hydroxyisobenzofuran-1,3-dione (0.773 g, 4.71 mmol, 1 eq) and 3-aminopiperidine-2,6-dione hydrochloride (0.775 g, 4.71 mmol, 1 eq) were dissolved in pyridine (19 mL) and heated to 110 C. for 16 hours. The mixture was concentrated under reduced pressure and purified by column chromatography (ISCO, 12 g silica column, 0-10% MeOH/DCM, 25 minute gradient) to give an off white solid (1.14 g, 4.16 mmol, 88%). 1H NMR (400 MHz, DMSO-d6) delta 11.19 (s, 1H), 11.07 (s, 1H), 7.65 (dd, J=8.3, 7.3 Hz, 1H), 7.31 (d, J=7.2 Hz, 1H), 7.24 (d, J=8.4 Hz, 1H), 5.07 (dd, J=12.8, 5.4 Hz, 1H), 2.88 (ddd, J=17.7, 14.2, 5.4 Hz, 1H), 2.63-2.50 (m, 2H), 2.11-1.95 (m, 1H). LCMS 275.11 (M+H)., 37418-88-5

37418-88-5 4-Hydroxyisobenzofuran-1,3-dione 96580, abenzofuran compound, is more and more widely used in various fields.

Reference£º
Patent; Dana-Farber Cancer Institute, Inc.; Bradner, James; Buckley, Dennis; Winter, Georg; (180 pag.)US2016/176916; (2016); A1;,
Benzofuran – Wikipedia
Benzofuran | C8H6O – PubChem