Diisopropylethylamine → HCID 25099554, compound

Participants

Reaction Conditions

Reaction Steps

A solution of 2-(3-fluoro-phenyl)-4-methyl-pyrimidine-5-carboxylic acid (379 mg, 1.63 mmol), HOTT (662 mg, 1.78 mmol), and DIPEA (800 μL, 4.58 mmol) in DMF (10 mL) is stirred at rt under N2 for 10 min. 5-Chloro-2-methyl-indol-1-ylamine (274 mg, 1.52 mmol) is 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 triturated in ether to afford 2-(3-fluoro-phenyl)-4-methyl-pyrimidine-5-carboxylic acid (5-chloro-2-methyl-indol-1-yl)-amide (93 mg, 16%) as a solid. MS: 395 (M+H). 1H NMR (300 MHz, DMSO-d6): δ 11.83 (s, 1H), 9.27 (s, 1H), 8.33 (d, 1H), 8.20-8.15 (m, 1H), 7.69-7.61 (m, 1H), 7.56 (d, 1H), 7.50-7.43 (m, 2H), 6.36 (s, 1H), 2.78 (s, 3H), 2.37 (s, 3H).

Provenance & Evidence