Diisopropylethylamine → 4-Methyl-2-pyridin-3-yl-pyrimidine-5-carboxylic acid (5-fluoro-2-methyl-indol-1-yl)-amide

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Reaction Steps

A solution of 4-methyl-2-pyridin-3-yl-pyrimidine-5-carboxylic acid (504 mg, 2.34 mmol), HCTU (1.06 g, 2.55 mmol), and DIPEA (1.11 mL, 6.30 mmol) in DMF (15 mL) is stirred at rt under N2 for 10 min. 5-Fluoro-2-methyl-indol-1-ylamine (346 mg, 2.11 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 4-methyl-2-pyridin-3-yl-pyrimidine-5-carboxylic acid (5-fluoro-2-methyl-indol-1-yl)-amide (82 mg, 11%) as a solid. MS: 362 (M+H). 1H NMR (300 MHz, DMSO-d6): δ 11.80 (s, 1H), 9.59 (d, 1H), 9.29 (s, 1H), 8.80-8.73 (m, 2H), 7.63 (dd, 1H), 7.22 (dd, 1H), 7.28 (dd, 1H), 6.97 (dt, 1H), 6.35 (s, 1H), 2.79 (s, 3H), 2.37 (s, 3H).

Provenance & Evidence