Diisopropylethylamine → HCID 25099475, compound

Participants

Reaction Steps

A solution of 2-pyridin-2-yl-pyrimidine-5-carboxylic acid (209 mg, 0.88 mmol), HOTT (435 mg, 1.17 mmol), and DIPEA (400 μL, 2.29 mmol) in DMF (10 mL) is stirred at rt under N2 for 20 min. 5-Fluoro-3-methyl-indol-1-ylamine (125 mg, 0.76 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-3-methyl-indol-1-yl)-amide (180 mg, 68%) as a solid. MS: 348 (M+H). 1H NMR (300 MHz, DMSO-d6): δ 12.12 (s, 1H), 9.47 (s, 2H), 8.82 (d, 1H), 8.51 (d, 1H), 8.05 (td, 1H), 7.62 (dd, 1H), 7.42 (dd, 1H), 7.35 (dd, 1H), 7.33 (s, 1H), 7.03 (td, 1H), 2.27 (s, 3H).

Provenance & Evidence