Diisopropylethylamine → 2-(3-Fluoro-phenyl)-4-methyl-pyrimidine-5-carboxylic acid (5-fluoro-3-methyl-pyrrolo[3,2-b]pyridin-1-yl)-amide

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Reaction Steps

A solution of 2-(3-fluoro-phenyl)-4-methyl-pyrimidine-5-carboxylic acid (1.34 mmol), 5-fluoro-3-methyl-pyrrolo[3,2-b]pyridin-1-ylamine (1.34 mmol), DIPEA (158 mg, 4.02 mmol) and HATU (1.60 mmol) in anhydrous DMF (8 mL) is stirred at 90° C. for 16 h. DMF is evaporated off in vacuo. The residue is dissolved in EtOAc (40 mL), and washed with water (3×20 mL) and brine (10 mL). The organic layer is dried (Na2SO4), filtered, and concentrated in vacuo. The residue is purified by silica gel chromatography eluting with 0-60% EtOAc in heptane to afford 2-(3-fluoro-phenyl)-4-methyl-pyrimidine-5-carboxylic acid (5-fluoro-3-methyl-pyrrolo[3,2-b]pyridin-1-yl)-amide (340 mg) as a solid. MS: 380 (M+H); 1H NMR (300 MHz, CDCl3): δ 2.36 (s, 3H), 2.86 (s, 3H), 6.84 (d, H), 7.12-7.35 (m, 2H), 7.52 (q, H), 7.63 (t, H), 8.10-8.43 (m, 2H), 8.98 (br, N—H).

Provenance & Evidence