Diisopropylethylamine → HCID 25099478, compound

Participants

Reaction Steps

A solution of 2-pyridin-2-yl-pyrimidine-5-carboxylic acid (485 mg, 2.04 mmol), HCTU (909 mg, 2.2 mmol), and DIPEA (1 mL, 5.72 mmol) in DMF (15 mL) is stirred at rt under N2 for 10 min. 5-Fluoro-2-methyl-indol-1-ylamine (299 mg, 1.82 mmol) is added. The resulting mixture is stirred at rt overnight. The mixture is 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 70% EtOAc in heptane to afford 2-pyridin-2-yl-pyrimidine-5-carboxylic acid (5-fluoro-2-methyl-indol-1-yl)-amide (112 mg, 18%) as a solid. MS: 348 (M+H). 1H NMR (300 MHz, DMSO-d6): δ 12.03 (s, 1H), 9.51 (s, 2H), 8.83 (d, 1H), 8.50 (d, 1H), 8.05 (dt, 1H), 7.62 (dd, 1H), 7.39 (dd, 1H), 7.28 (dd, 1H), 6.94 (dt, 1H), 6.35 (s, 1H), 2.33 (s, 3H).

Provenance & Evidence