[1-(4-bromo-2-methoxyphenyl)cyclobutyl]methanol

Conditions: temp:80.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: To a mixture of [1-(4-bromo-2-methoxyphenyl)cyclobutyl]methanol (180 mg, 0.660 mmol) in dioxane (10 mL) and water (4 mL) was added methyl 6-chloro-5-(5,5-dimethyl-1,3,2-dioxaborinan-2-yl)-1H-indole-3-carboxylate (213 mg, 0.660 mmol), Pd (dppf)Cl2 (48 mg, 0.070 mmol) and potassium carbonate (273 mg, 2.00 mmol). The reaction mixture was purged with nitrogen for 3 minutes and stirred at 80° C. for 2 hours. The mixture was extracted with dichloromethane. The organic phases were combined, dried over sodium sulfate, filtered, and concentrated in vacuo to give the title compound (220 mg, 83%) as a brown solid. It was used for next step without further purification. The reaction mixture was purged with nitrogen for 3 minutes The mixture was extracted with dichloromethane dried over sodium sulfate filtered concentrated in vacuo

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

Procedure: To a mixture of 1-(4-bromo-2-methoxyphenyl)cyclobutanecarboxylic acid (320 mg, 1.12 mmol) in dry tetrahydrofuran (10 mL) was added borane-tetrahydrofuran (0.67 mL, 6.7 mmol) dropwise. The mixture was stirred at room temperature for 3 hours. The reaction mixture was quenched by water and extracted with dichloromethane. The organic layers were combined, dried over sodium sulfate, and concentrated to give the title compound (280 mg, 92%) as a colorless oil. 1H NMR (500 MHz, DMSO-d6) δ 7.05 (m, 2H), 6.86 (d, 1H), 4.57 (t, 1H), 3.73 (s, 3H), 3.55 (d, 2H), 2.05-2.17 (m, 4H), 1.95 (m, 1H), 1.69 (m, 1H). The reaction mixture was quenched by water extracted with dichloromethane dried over sodium sulfate concentrated

Conditions: temp:80.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: To a mixture of [1-(4-bromo-2-methoxyphenyl)cyclobutyl]methanol (180 mg, 0.660 mmol) in dioxane (10 mL) and water (4 mL) was added methyl 6-chloro-5-(5,5-dimethyl-1,3,2-dioxaborinan-2-yl)-1H-indole-3-carboxylate (213 mg, 0.660 mmol), Pd (dppf)Cl2 (48 mg, 0.070 mmol) and potassium carbonate (273 mg, 2.00 mmol). The reaction mixture was purged with nitrogen for 3 minutes and stirred at 80° C. for 2 hours. The mixture was extracted with dichloromethane. The organic phases were combined, dried over sodium sulfate, filtered, and concentrated in vacuo to give the title compound (220 mg, 83%) as a brown solid. It was used for next step without further purification. The reaction mixture was purged with nitrogen for 3 minutes The mixture was extracted with dichloromethane dried over sodium sulfate filtered concentrated in vacuo

Conditions: temp:80.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: To a mixture of [1-(4-bromo-2-methoxyphenyl)cyclobutyl]methanol (180 mg, 0.660 mmol) in dioxane (10 mL) and water (4 mL) was added methyl 6-chloro-5-(5,5-dimethyl-1,3,2-dioxaborinan-2-yl)-1H-indole-3-carboxylate (213 mg, 0.660 mmol), Pd (dppf)Cl2 (48 mg, 0.070 mmol) and potassium carbonate (273 mg, 2.00 mmol). The reaction mixture was purged with nitrogen for 3 minutes and stirred at 80° C. for 2 hours. The mixture was extracted with dichloromethane. The organic phases were combined, dried over sodium sulfate, filtered, and concentrated in vacuo to give the title compound (220 mg, 83%) as a brown solid. It was used for next step without further purification. The reaction mixture was purged with nitrogen for 3 minutes The mixture was extracted with dichloromethane dried over sodium sulfate filtered concentrated in vacuo

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

Procedure: To a mixture of 1-(4-bromo-2-methoxyphenyl)cyclobutanecarboxylic acid (320 mg, 1.12 mmol) in dry tetrahydrofuran (10 mL) was added borane-tetrahydrofuran (0.67 mL, 6.7 mmol) dropwise. The mixture was stirred at room temperature for 3 hours. The reaction mixture was quenched by water and extracted with dichloromethane. The organic layers were combined, dried over sodium sulfate, and concentrated to give the title compound (280 mg, 92%) as a colorless oil. 1H NMR (500 MHz, DMSO-d6) δ 7.05 (m, 2H), 6.86 (d, 1H), 4.57 (t, 1H), 3.73 (s, 3H), 3.55 (d, 2H), 2.05-2.17 (m, 4H), 1.95 (m, 1H), 1.69 (m, 1H). The reaction mixture was quenched by water extracted with dichloromethane dried over sodium sulfate concentrated

Conditions: temp:80.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: To a mixture of [1-(4-bromo-2-methoxyphenyl)cyclobutyl]methanol (180 mg, 0.660 mmol) in dioxane (10 mL) and water (4 mL) was added methyl 6-chloro-5-(5,5-dimethyl-1,3,2-dioxaborinan-2-yl)-1H-indole-3-carboxylate (213 mg, 0.660 mmol), Pd (dppf)Cl2 (48 mg, 0.070 mmol) and potassium carbonate (273 mg, 2.00 mmol). The reaction mixture was purged with nitrogen for 3 minutes and stirred at 80° C. for 2 hours. The mixture was extracted with dichloromethane. The organic phases were combined, dried over sodium sulfate, filtered, and concentrated in vacuo to give the title compound (220 mg, 83%) as a brown solid. It was used for next step without further purification. The reaction mixture was purged with nitrogen for 3 minutes The mixture was extracted with dichloromethane dried over sodium sulfate filtered concentrated in vacuo

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

Procedure: To a mixture of 1-(4-bromo-2-methoxyphenyl)cyclobutanecarboxylic acid (320 mg, 1.12 mmol) in dry tetrahydrofuran (10 mL) was added borane-tetrahydrofuran (0.67 mL, 6.7 mmol) dropwise. The mixture was stirred at room temperature for 3 hours. The reaction mixture was quenched by water and extracted with dichloromethane. The organic layers were combined, dried over sodium sulfate, and concentrated to give the title compound (280 mg, 92%) as a colorless oil. 1H NMR (500 MHz, DMSO-d6) δ 7.05 (m, 2H), 6.86 (d, 1H), 4.57 (t, 1H), 3.73 (s, 3H), 3.55 (d, 2H), 2.05-2.17 (m, 4H), 1.95 (m, 1H), 1.69 (m, 1H). The reaction mixture was quenched by water extracted with dichloromethane dried over sodium sulfate concentrated

Conditions: temp:80.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: To a mixture of [1-(4-bromo-2-methoxyphenyl)cyclobutyl]methanol (180 mg, 0.660 mmol) in dioxane (10 mL) and water (4 mL) was added methyl 6-chloro-5-(5,5-dimethyl-1,3,2-dioxaborinan-2-yl)-1H-indole-3-carboxylate (213 mg, 0.660 mmol), Pd (dppf)Cl2 (48 mg, 0.070 mmol) and potassium carbonate (273 mg, 2.00 mmol). The reaction mixture was purged with nitrogen for 3 minutes and stirred at 80° C. for 2 hours. The mixture was extracted with dichloromethane. The organic phases were combined, dried over sodium sulfate, filtered, and concentrated in vacuo to give the title compound (220 mg, 83%) as a brown solid. It was used for next step without further purification. The reaction mixture was purged with nitrogen for 3 minutes The mixture was extracted with dichloromethane dried over sodium sulfate filtered concentrated in vacuo

Conditions: temp:80.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: To a mixture of [1-(4-bromo-2-methoxyphenyl)cyclobutyl]methanol (180 mg, 0.660 mmol) in dioxane (10 mL) and water (4 mL) was added methyl 6-chloro-5-(5,5-dimethyl-1,3,2-dioxaborinan-2-yl)-1H-indole-3-carboxylate (213 mg, 0.660 mmol), Pd (dppf)Cl2 (48 mg, 0.070 mmol) and potassium carbonate (273 mg, 2.00 mmol). The reaction mixture was purged with nitrogen for 3 minutes and stirred at 80° C. for 2 hours. The mixture was extracted with dichloromethane. The organic phases were combined, dried over sodium sulfate, filtered, and concentrated in vacuo to give the title compound (220 mg, 83%) as a brown solid. It was used for next step without further purification. The reaction mixture was purged with nitrogen for 3 minutes The mixture was extracted with dichloromethane dried over sodium sulfate filtered concentrated in vacuo

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

Procedure: To a mixture of 1-(4-bromo-2-methoxyphenyl)cyclobutanecarboxylic acid (320 mg, 1.12 mmol) in dry tetrahydrofuran (10 mL) was added borane-tetrahydrofuran (0.67 mL, 6.7 mmol) dropwise. The mixture was stirred at room temperature for 3 hours. The reaction mixture was quenched by water and extracted with dichloromethane. The organic layers were combined, dried over sodium sulfate, and concentrated to give the title compound (280 mg, 92%) as a colorless oil. 1H NMR (500 MHz, DMSO-d6) δ 7.05 (m, 2H), 6.86 (d, 1H), 4.57 (t, 1H), 3.73 (s, 3H), 3.55 (d, 2H), 2.05-2.17 (m, 4H), 1.95 (m, 1H), 1.69 (m, 1H). The reaction mixture was quenched by water extracted with dichloromethane dried over sodium sulfate concentrated

Conditions: temp:80.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: To a mixture of [1-(4-bromo-2-methoxyphenyl)cyclobutyl]methanol (180 mg, 0.660 mmol) in dioxane (10 mL) and water (4 mL) was added methyl 6-chloro-5-(5,5-dimethyl-1,3,2-dioxaborinan-2-yl)-1H-indole-3-carboxylate (213 mg, 0.660 mmol), Pd (dppf)Cl2 (48 mg, 0.070 mmol) and potassium carbonate (273 mg, 2.00 mmol). The reaction mixture was purged with nitrogen for 3 minutes and stirred at 80° C. for 2 hours. The mixture was extracted with dichloromethane. The organic phases were combined, dried over sodium sulfate, filtered, and concentrated in vacuo to give the title compound (220 mg, 83%) as a brown solid. It was used for next step without further purification. The reaction mixture was purged with nitrogen for 3 minutes The mixture was extracted with dichloromethane dried over sodium sulfate filtered concentrated in vacuo

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

Procedure: To a mixture of 1-(4-bromo-2-methoxyphenyl)cyclobutanecarboxylic acid (320 mg, 1.12 mmol) in dry tetrahydrofuran (10 mL) was added borane-tetrahydrofuran (0.67 mL, 6.7 mmol) dropwise. The mixture was stirred at room temperature for 3 hours. The reaction mixture was quenched by water and extracted with dichloromethane. The organic layers were combined, dried over sodium sulfate, and concentrated to give the title compound (280 mg, 92%) as a colorless oil. 1H NMR (500 MHz, DMSO-d6) δ 7.05 (m, 2H), 6.86 (d, 1H), 4.57 (t, 1H), 3.73 (s, 3H), 3.55 (d, 2H), 2.05-2.17 (m, 4H), 1.95 (m, 1H), 1.69 (m, 1H). The reaction mixture was quenched by water extracted with dichloromethane dried over sodium sulfate concentrated