Acetic Acid → HCID 58154577, compound

Participants

Reaction Steps

To a mixture of 2-(3-(trifluoromethyl)phenyl)quinolin-8-amine (200 mg, 0.7 mmol), 3-pyridinecarbaldehyde (150 mg, 1.4 mmol) and acetic acid (84 mg, 1.4 mmol) in methanol (10 mL) was added NaCNBH3 (88 mg, 1.4 mmol) in portions at room temperature, then the reaction was stirred at room temperature for 5 h. The reaction was concentrated in vacuo, the residue was taken up in DCM, The solution was washed with water (1×50 mL), treated with active carbon and Na2SO4, filtered through a silica gel pad, and the pad was washed with CH2Cl2. The organic solutions were combined and concentrated in vacuo, triturated with a mixture of ethyl acetate/pentane and filtered to give N-(pyridin-3-ylmethyl)-2-(3-(trifluoromethyl)phenyl)quinolin-8-amine as a yellow solid (220 mg, yield 83%) MS (ESI) calcd for C22H16F3N3 (m/z): 379.13. found: 380 [M+1].

Provenance & Evidence