[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.
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