Diisopropylethylamine → 2-(3-Fluoro-phenyl)-pyrimidine-5-carboxylic acid (5-fluoro-2-methyl-indol-1-yl)amide

Participants

Reaction Conditions

Reaction Steps

A solution of 2-(3-fluoro-phenyl)-pyrimidine-5-carboxylic acid (389 mg, 1.78 mmol), HOAt (290 mg, 2.13 mmol), and HATU (811 mg, 2.13 mmol) in DMF (20 mL) is stirred at rt under N2 for 20 min. 5-Fluoro-2-methyl-indol-1-ylamine (290 mg, 1.77 mmol) and DIPEA (450 μL, 2.58 mmol) are added. The resulting mixture is stirred at 80° C. overnight. The mixture is cooled and portioned between EtOAc and water. The organic phase is separated, washed with saturated aqueous NaHCO3, water and brine, dried (MgSO4), filtered and concentrated in vacuo. The residue is purified by silica gel chromatography eluting with 25% DCM in heptane to afford 2-(3-fluoro-phenyl)-pyrimidine-5-carboxylic acid (5-fluoro-2-methyl-indol-1-yl)amide (300 mg, 47%) as a solid. MS: 365 (M+H). 1H NMR (300 MHz, CDCl3): δ 9.23 (s, 1H), 8.76 (s, 1H), 8.35-8.22 (m, 2H), 7.54-7.45 (m, 1H), 7.19-6.86 (m, 5H), 6.25 (s, 1H), 2.29 (s, 3H).

Provenance & Evidence