ethyl (3S)-piperidine-3-carboxylate;hydrochloride

反応条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: A solution of ethyl (3S)-piperidine-3-carboxylate hydrochloride (0.1 g, 0.0005 mol), bromobenzene (0.16 g, 0.0010 mol) and potassium tert-butoxide (0.12 g, 0.0010 mol) in dimethyl sulfoxide (4 mL, 0.06 mol) was heated at 200° C. for 10 min. under microwave irradiation. The crude (3S)-1-phenylpiperidine-3-carboxylic acid was subjected to BOP-mediated coupling by using a procedure that was analogous to that described for the synthesis of example 129, step 3. LCMS: m/z 301.2 (M+H)+. that described for the synthesis of example 129, step 3

反応条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: A mixture of 4-(4-bromo-3-fluorophenyl)pyridine (190 mg, 0.00075 mol), ethyl (3S)-piperidine-3-carboxylate hydrochloride (180 mg, 0.00090 mol), sodium tert-butoxide (140 mg, 0.0015 mol), palladium acetate (5 mg, 0.00002 mol) and 2-(di-tert-butylphosphino)biphenyl (7 mg, 0.00002 mol) was evacuated and charged with nitrogen and 1,4-dioxane (5 mL, 0.06 mol). The resulting mixture was refluxed overnight. After cooling to ambient temperature, the mixture was filtered and the filtrate was adjusted with TFA to pH=7.0 and purified by CombiFlash (ethyl acetate in hexanes: 60%) to afford the desired product. LCMS: m/z 329.2 (M+H)+. was evacuated The resulting mixture was refluxed overnight the mixture was filtered purified by CombiFlash (ethyl acetate in hexanes: 60%)

反応条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: A solution of ethyl (3S)-piperidine-3-carboxylate hydrochloride (0.1 g, 0.0005 mol), bromobenzene (0.16 g, 0.0010 mol) and potassium tert-butoxide (0.12 g, 0.0010 mol) in dimethyl sulfoxide (4 mL, 0.06 mol) was heated at 200° C. for 10 min. under microwave irradiation. The crude (3S)-1-phenylpiperidine-3-carboxylic acid was subjected to BOP-mediated coupling by using a procedure that was analogous to that described for the synthesis of example 129, step 3. LCMS: m/z 301.2 (M+H)+. that described for the synthesis of example 129, step 3

反応条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: A mixture of 4-(4-bromo-3-fluorophenyl)pyridine (190 mg, 0.00075 mol), ethyl (3S)-piperidine-3-carboxylate hydrochloride (180 mg, 0.00090 mol), sodium tert-butoxide (140 mg, 0.0015, mol), palladium acetate (5 mg, 0.00002 mol) and 2-(di-tert-butylphosphino)biphenyl (7 mg, 0.00002 mol) was evacuated and charged with nitrogen and 1,4-dioxane (5 mL, 0.06 mol). The resulting mixture was refluxed overnight. After cooling to ambient temperature, the mixture was filtered and the filtrate was adjusted with TFA to pH=7.0 and purified by CombiFlash (ethyl acetate in hexanes: 60%) to afford the desired product. LCMS: m/z 329.2 (M+H)+. was evacuated The resulting mixture was refluxed overnight the mixture was filtered purified by CombiFlash (ethyl acetate in hexanes: 60%)

反応条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: A solution of ethyl (3S)-piperidine-3-carboxylate hydrochloride (0.1 g, 0.0005 mol), bromobenzene (0.16 g, 0.0010 mol) and potassium tert-butoxide (0.12 g, 0.0010 mol) in dimethyl sulfoxide (4 mL, 0.06 mol) was heated at 200° C. for 10 min. under microwave irradiation. The crude (3S)-1-phenylpiperidine-3-carboxylic acid was subjected to BOP-mediated coupling by using a procedure that was analogous to that described for the synthesis of example 129, step 3. LCMS: m/z 301.2 (M+H)+. that described for the synthesis of example 129, step 3

反応条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: A mixture of 4-(4-bromo-3-fluorophenyl)pyridine (190 mg, 0.00075 mol), ethyl (3S)-piperidine-3-carboxylate hydrochloride (180 mg, 0.00090 mol), sodium tert-butoxide (140 mg, 0.0015 mol), palladium acetate (5 mg, 0.00002 mol) and 2-(di-tert-butylphosphino)biphenyl (7 mg, 0.00002 mol) was evacuated and charged with nitrogen and 1,4-dioxane (5 mL, 0.06 mol). The resulting mixture was refluxed overnight. After cooling to ambient temperature, the mixture was filtered and the filtrate was adjusted with TFA to pH=7.0 and purified by CombiFlash (ethyl acetate in hexanes: 60%) to afford the desired product. LCMS: m/z 329.2 (M+H)+. was evacuated The resulting mixture was refluxed overnight the mixture was filtered purified by CombiFlash (ethyl acetate in hexanes: 60%)