Diisopropylethylamine → N-((2'-fluoro-3-methyl-2,4'-bipyridin-5-yl)methyl)-5-(3-fluorophenyl)picolinamide

Participants

Reaction Steps

To a mixture of 5-(3-fluorophenyl)picolinic acid 6-7 (32 mg, 0.15 mmol), (2′-fluoro-3-methyl-2,4′-bipyridin-5-yl)methanamine 30-5 (28 mg, 0.13 mmol) and O-(7-azabenzotriazol-1-yl)-N,N,N′,N′-tetramethyluroniumhexafluorophosphate (HATU) (60 mg, 0.16 mmol) in DMF (1.0 mL) was added DIEA (0.068 mL, 0.39 mmol) at room temperature. The mixture was stirred at room temperature for 2 hours. The reaction mixture was diluted into DMSO and purified by HPLC to give N-((2′-fluoro-3-methyl-2,4′-bipyridin-5-yl)methyl)-5-(3-fluorophenyl)picolinamide 30 as a white solid. MS m/z 417.2 (M+1). 1H NMR 400 MHz (DMSO-d6) δ 9.54 (t, 1H), 8.95 (dd, 1H), 8.47 (d, 1H), 8.29 (m, 2H), 8.07 (dd, 1H), 7.69 (m, 2H), 7.63 (m, 1H), 7.55 (m, 1H), 7.48 (m, 1H), 7.29 (m, 2H), 4.52 (d, 2H), 2.28 (s, 3H).

Provenance & Evidence