Potassium Carbonate → HCID 16065530, compound

Participants

Reaction Steps

3-(bromomethyl)-2-phenyl-N-[(1S)-1-phenylpropyl]quinoline-4-carboxamide (8) (150 mg, 0.33 mmol) was dissolved in CH3CN (2 mL) under N2 and to this, with stirring, was added K2CO3 (140 mg, 0.99 mmol), then 4-mercaptopyridine (40 mg, 0.36 mmol). The suspension was allowed to stir overnight; concentrated; diluted with EtOAc; washed with 0.5 N NaOH, then H2O; dried over Na2SO4; filtered, and concentrated under reduced pressure. The residue was purified by silica gel chromatography (EtOAc/CH2Cl2) to afford the desired product as oil (120 mg, 74% yield). 1H NMR (300 MHz, CDCl3, 52° C.) δ 8.30 (s, 2H), 8.14 (d, J=8.4 Hz, 1H), 7.80 (d, J=7.2 Hz, 1H), 7.76-7.69 (m, 1H), 7.62-7.49 (m, 3H), 7.43-7.37 (m, 3H), 7.35-7.28 (m, 2H), 7.25-7.19 (m, 3H), 6.80 (d, J=4.4 Hz, 2H), 6.37 (d, J=7.9 Hz, 1H), 5.21 (q, J=7.6 Hz, 1H), 4.36-4.23 (m, 2H), 2.08-1.82 (m, 2H), 0.95 (t, J=7.4 Hz, 3H); HRMS m/z 490.1931, calcd 490.1953.

Provenance & Evidence