Dimethylformamide → HCID 67497264, compound

Participants

Reaction Conditions

Reaction Steps

To a 5 mL flask was added (S)—N-(3-bromophenyl)-3-phenyl-2-(thiazol-4-ylmethylamino)propanamide 39.B (50 mg, 0.12 mmol), 2-methylpyridin-4-yl boronic acid (21 mg, 0.16 mmol, available from Combi-Phos), tetrakis(triphenylphosphine)palladium(0) (28 mg, 0.024 mmol), DMF (0.5 mL) and saturated aqueous K2CO3 (0.5 mL). The reaction mixture was stirred at 100° C. for 2 hours. The mixture was diluted with methanol (3 mL), filtered and purified directly on reverse phase preparative HPLC to afford (2S)—N-(3-(2-methylpyridin-4-yl)phenyl)-3-phenyl-2-(thiazol-4-ylmethylamino)propanamide 39 (27.2 mg, 53% yield) as a white solid. LCMS ESI (pos.) m/e: 429.1. (M+1). 1H NMR (500 MHz, MeOH-D4) δ ppm 9.12 (d, J=1.96 Hz, 1H), 8.74 (d, J=6.36 Hz, 1H), 8.19 (s, 1H), 8.12 (dd, J=6.36, 1.96 Hz, 1H), 8.11 (t, J=1.71 Hz, 1H), 7.82 (d, J=1.96 Hz, 1H), 7.68-7.75 (m, 1H), 7.58 (t, J=7.83 Hz, 1H), 7.52-7.56 (m, 1H), 7.23-7.37 (m, 5H), 4.53 (d, J=4.65 Hz, 2H), 4.35 (dd, J=9.29, 5.87 Hz, 1H), 3.46 (dd, J=13.45, 5.87 Hz, 1H), 3.28 (dd, J=13.45, 9.29 Hz, 1H), 2.88 (s, 3H).

Provenance & Evidence