3-(4-bromo-2-methoxyphenyl)oxetan-3-ol

Conditions: temp:115.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: To a solution of methyl 6-chloro-5-(5,5-dimethyl-1,3,2-dioxaborinan-2-yl)-1H-indole-3-carboxylate (70 mg, 0.27 mmol) and 3-(4-bromo-2-methoxyphenyl)oxetan-3-ol (96 mg, 0.30 mmol) in toluene (1.2 mL), ethanol (0.6 mL), and tetrahydrofuran (0.6 mL) followed by the addition of 2M potassium carbonate aqueous (0.6 mL, 1 mmol). Nitrogen was bubbled through the reaction for 5 minutes then [1,1′-bis(diphenylphosphino)ferrocene]dichloro palladium, dichloromethane (25 mg, 0.031 mmol) was added and the reaction heated to 115° C. for 16 hours. The reaction was then cooled to room temperature and filtered through a pad of celite washing with ethyl acetate. The filtrate was concentrated under reduced pressure and passed through silica yielding 104 mg of the title compound that was brought forward without further purification. MS (ES+) 386.1 (M−H)+. Nitrogen was bubbled through the reaction for 5 minutes The reaction was then cooled to room temperature filtered through a pad of celite washing with ethyl acetate The filtrate was concentrated under reduced pressure was brought forward without further purification

Conditions: temp:115.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: To a solution of methyl 6-chloro-5-(5,5-dimethyl-1,3,2-dioxaborinan-2-yl)-1H-indole-3-carboxylate (70 mg, 0.27 mmol) and 3-(4-bromo-2-methoxyphenyl)oxetan-3-ol (96 mg, 0.30 mmol) in toluene (1.2 mL), ethanol (0.6 mL), and tetrahydrofuran (0.6 mL) followed by the addition of 2M potassium carbonate aqueous (0.6 mL, 1 mmol). Nitrogen was bubbled through the reaction for 5 minutes then [1,1′-bis(diphenylphosphino)ferrocene]dichloro palladium, dichloromethane (25 mg, 0.031 mmol) was added and the reaction heated to 115° C. for 16 hours. The reaction was then cooled to room temperature and filtered through a pad of celite washing with ethyl acetate. The filtrate was concentrated under reduced pressure and passed through silica yielding 104 mg of the title compound that was brought forward without further purification. MS (ES+) 386.1 (M−H)+. Nitrogen was bubbled through the reaction for 5 minutes The reaction was then cooled to room temperature filtered through a pad of celite washing with ethyl acetate The filtrate was concentrated under reduced pressure was brought forward without further purification

Conditions: temp:115.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: To a solution of methyl 6-chloro-5-(5,5-dimethyl-1,3,2-dioxaborinan-2-yl)-1H-indole-3-carboxylate (70 mg, 0.27 mmol) and 3-(4-bromo-2-methoxyphenyl)oxetan-3-ol (96 mg, 0.30 mmol) in toluene (1.2 mL), ethanol (0.6 mL), and tetrahydrofuran (0.6 mL) followed by the addition of 2M potassium carbonate aqueous (0.6 mL, 1 mmol). Nitrogen was bubbled through the reaction for 5 minutes then [1,1′-bis(diphenylphosphino)ferrocene]dichloro palladium, dichloromethane (25 mg, 0.031 mmol) was added and the reaction heated to 115° C. for 16 hours. The reaction was then cooled to room temperature and filtered through a pad of celite washing with ethyl acetate. The filtrate was concentrated under reduced pressure and passed through silica yielding 104 mg of the title compound that was brought forward without further purification. MS (ES+) 386.1 (M−H)+. Nitrogen was bubbled through the reaction for 5 minutes The reaction was then cooled to room temperature filtered through a pad of celite washing with ethyl acetate The filtrate was concentrated under reduced pressure was brought forward without further purification

Conditions: temp:115.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: To a solution of methyl 6-chloro-5-(5,5-dimethyl-1,3,2-dioxaborinan-2-yl)-1H-indole-3-carboxylate (70 mg, 0.27 mmol) and 3-(4-bromo-2-methoxyphenyl)oxetan-3-ol (96 mg, 0.30 mmol) in toluene (1.2 mL), ethanol (0.6 mL), and tetrahydrofuran (0.6 mL) followed by the addition of 2M potassium carbonate aqueous (0.6 mL, 1 mmol). Nitrogen was bubbled through the reaction for 5 minutes then [1,1′-bis(diphenylphosphino)ferrocene]dichloro palladium, dichloromethane (25 mg, 0.031 mmol) was added and the reaction heated to 115° C. for 16 hours. The reaction was then cooled to room temperature and filtered through a pad of celite washing with ethyl acetate. The filtrate was concentrated under reduced pressure and passed through silica yielding 104 mg of the title compound that was brought forward without further purification. MS (ES+) 386.1 (M−H)+. Nitrogen was bubbled through the reaction for 5 minutes The reaction was then cooled to room temperature filtered through a pad of celite washing with ethyl acetate The filtrate was concentrated under reduced pressure was brought forward without further purification

Conditions: temp:115.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: To a solution of methyl 6-chloro-5-(5,5-dimethyl-1,3,2-dioxaborinan-2-yl)-1H-indole-3-carboxylate (70 mg, 0.27 mmol) and 3-(4-bromo-2-methoxyphenyl)oxetan-3-ol (96 mg, 0.30 mmol) in toluene (1.2 mL), ethanol (0.6 mL), and tetrahydrofuran (0.6 mL) followed by the addition of 2M potassium carbonate aqueous (0.6 mL, 1 mmol). Nitrogen was bubbled through the reaction for 5 minutes then [1,1′-bis(diphenylphosphino)ferrocene]dichloro palladium, dichloromethane (25 mg, 0.031 mmol) was added and the reaction heated to 115° C. for 16 hours. The reaction was then cooled to room temperature and filtered through a pad of celite washing with ethyl acetate. The filtrate was concentrated under reduced pressure and passed through silica yielding 104 mg of the title compound that was brought forward without further purification. MS (ES+) 386.1 (M−H)+. Nitrogen was bubbled through the reaction for 5 minutes The reaction was then cooled to room temperature filtered through a pad of celite washing with ethyl acetate The filtrate was concentrated under reduced pressure was brought forward without further purification