[CH2:1]([NH2:4])[CH2:2][CH3:3].[NH:5]1[C:13]2[C:8](=[CH:9][CH:10]=[CH:11][C:12]=2[CH:14]=O)[CH:7]=[CH:6]1.C(O)(=O)C.[BH4-].[Na+]>C1(C)C=CC=CC=1.CO.O>[NH:4]1[C:14]2[C:3](=[CH:9][CH:10]=[CH:11][C:12]=2[CH2:13][NH:5][CH2:6][CH2:7][CH3:8])[CH:2]=[CH:1]1Add propyl amine (3.66 g, 62.07 mmol) to a solution of indole-7-carboxaldehyde (3.0 g, 20.68 mmol) and acetic acid (2.65 ml, 41.3 mmol) in toluene (100 ml). Heat at reflux constantly removing water with a Dean Stark apparatus. Concentrate the reaction under reduced pressure and re-dissolve in methanol. Gently add sodium borohydride (0.39 g, 10.34 mmol). Stir for 1 hour at room temperature, concentrate, and partition between ethyl acetate and saturated aqueous sodium bicarbonate. Concentrate the organic layers under reduced pressure. Compound carried onto next step without purification.
불러오는 중…
