7-methoxy-1-benzofuran

Conditions: temp:0.00; pressure:0.00; stir:

Conditions: temp:0.00; pressure:0.00; stir:

Conditions: temp:0.00; pressure:0.00; stir:

Conditions: temp:0.00; pressure:0.00; stir:

Conditions: temp:0.00; pressure:0.00; stir:

Conditions: temp:0.00; pressure:0.00; stir:

Conditions: temp:-78.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: n-Butyllithium (1.6M in hexanes, 10.2 ml) was added dropwise to a cooled (-78° C.) solution of 7-methoxybenzofuran (2.0 g) in tetrahydrofuran (40 ml) under an inert atmosphere. Methyl disulfide (1.46 ml) was added and the reaction mixture was stirred at -78° C. for 30 minutes, then at room temperature for 1 h. Water was added and the tetrahydrofuran was removed in vacuo. The aqueous residue was extracted with ether (3×100 ml) and the combined organic phases were washed with water (100 ml) and dried over sodium sulfate. The solvent was removed in vacuo to afford the title compound as a yellow oil (2.73 g). at room temperature for 1 h the tetrahydrofuran was removed in vacuo The aqueous residue was extracted with ether (3×100 ml) the combined organic phases were washed with water (100 ml) dried over sodium sulfate The solvent was removed in vacuo

Conditions: temp:-60.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: To a stirred solution of 7-methoxybenzofuran (2.0 g) in tetrahydrofuran (30 ml) cooled to -60° C. under an atmosphere of nitrogen was added dropwise n-butyllithium (1.6M in hexanes, 8.9 ml). After stirring at -60° C. for 10 minutes, magnesium bromide diethyl etherate (3.8 g) was added in single portion and the reaction mixture stirred at -50° C. for 10 minutes. After cooling to -78° C., cyclopropane carboxaldehyde (1.0 ml) was added in a single portion and the mixture allowed to warm slowly to room temperature and stirred for 1 h. Water (2 ml) was added and the tetrahydrofuran removed in vacuo. The residue was partitioned between ethyl acetate (50 ml) and water (50 ml); the aqueous layer was extracted with ethyl acetate (50 ml); the organic layers were combined, dried over magnesium sulfate, filtered and concentrated in vacuo. Purification by flash chromatography on silica eluting with 0-5% methanol in dichloromethane afforded the title compound as a yellow gum (1.88 g). the reaction mixture stirred at -50° C. for 10 minutes After cooling to -78° C. to warm slowly to room temperature stirred for 1 h the tetrahydrofuran removed in vacuo The residue was partitioned between ethyl acetate (50 ml) and water (50 ml) the aqueous layer was extracted with ethyl acetate (50 ml) dried over magnesium sulfate filtered concentrated in vacuo Purification by flash chromatography on silica eluting with 0-5% methanol in dichloromethane

Conditions: temp:-60.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: To a stirred solution of 7-methoxybenzofuran (2.0 g) in tetrahydrofuran (30 ml) cooled to -60° C. under an atmosphere of nitrogen was added dropwise n-butyllithium (1.6M in hexanes, 8.9 ml). After stirring at -60° C. for 10 minutes, magnesium bromide diethyl etherate (3.8 g) was added in single portion and the reaction mixture stirred at -50° C. for 10 minutes. After cooling to -78° C., cyclopropane carboxaldehyde (1.0 ml) was added in a single portion and the mixture allowed to warm slowly to room temperature and stirred for 1 h. Water (2 ml) was added and the tetrahydrofuran removed in vacuo. The residue was partitioned between ethyl acetate (50 ml) and water (50 ml); the aqueous layer was extracted with ethyl acetate (50 ml); the organic layers were combined, dried over magnesium sulfate, filtered and concentrated in vacuo. Purification by flash chromatography on silica eluting with 0-5% methanol in dichloromethane afforded the title compound as a yellow gum (1.88 g). the reaction mixture stirred at -50° C. for 10 minutes After cooling to -78° C. to warm slowly to room temperature stirred for 1 h the tetrahydrofuran removed in vacuo The residue was partitioned between ethyl acetate (50 ml) and water (50 ml) the aqueous layer was extracted with ethyl acetate (50 ml) dried over magnesium sulfate filtered concentrated in vacuo Purification by flash chromatography on silica eluting with 0-5% methanol in dichloromethane

Conditions: temp:-78.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: To a stirred solution of 7-methoxybenzofuran (3.0 g) in tetrahydrofuran (60 ml) cooled to -78° C. under an atmosphere of nitrogen was added dropwise n-butyllithium (1.6M in hexanes, 15.2 ml). After stirring at -78° C. for 30 minutes, magnesium bromide diethyl etherate (6.3 g) was added in single portion and the reaction mixture allowed to warm to 0° C. and stirred for 30 minutes. Cyclopropyl cyanide (1.8 ml) was then added dropwise and the mixture allowed to warm slowly to room temperature and stirred for 18 h. Aqueous hydrochloric acid (2M, 50 ml) was added to the reaction mixture and stirring continued for 1 h. The mixture was extracted with ethyl acetate (250 ml), then washed successively with water (50 ml) and brine (50 ml). The organic layer was separated and dried over magnesium sulfate, filtered and concentrated in vacuo. Purification by flash chromatography on silica eluting with 5-20% ethyl acetate in hexane afforded the title compound as a yellow oil (0.96 g). to warm to 0° C. stirred for 30 minutes to warm slowly to room temperature stirred for 18 h stirring continued for 1 h The mixture was extracted with ethyl acetate (250 ml) washed successively with water (50 ml) and brine (50 ml) The organic layer was separated dried over magnesium sulfate filtered concentrated in vacuo Purification by flash chromatography on silica eluting with 5-20% ethyl acetate in hexane

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: Prepared according to a procedure analogous to that described for 7-chloro-2-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-1H-indole using 7-methoxy-benzofuran. Prepared

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: Prepared according to a procedure analogous to that described for 7-chloro-2-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-1H-indole using 7-methoxy-benzofuran. Prepared