Diisopropylethylamine → HCID 25099694, compound

Participants

Reaction Steps

A solution of 4-methyl-2-pyridin-2-yl-pyrimidine-5-carboxylic acid (748 mg, 3.48 mmol) in DMF (30 mL) is treated with HATU (1.3 g, 3.48 mmol) and DIPEA (1.2 mL, 6.96 mmol), and the mixture is stirred at rt for 30 min. 1-(1-Amino-5-fluoroindol-3-yl)-2-methyl-propan-2-ol (2.9 mmol) is added and the mixture is stirred at 80° C. for 12 h. The mixture is diluted with EtOAc, washed with saturated aqueous NH4Cl and saturated aqueous Na2CO3, dried (Na2SO4), filtered and concentrated in vacuo to afford 4-methyl-2-pyridin-2-yl-pyrimidine-5-carboxylic acid [5-fluoro-3-(2-hydroxy-2-methyl-propyl)-indol-1-yl]-amide (990 mg, 81%). MS: 420 (M+H); 1H NMR (300 MHz, DMSO-d6): δ 1.13 (s, 6H), 2.75 (s, 2H), 2.85 (s, 3H), 6.84 (m, 1H), 7.24 (m, 1H), 7.37 (m, 1H), 7.53 (m, 1H), 7.95 (s, 1H), 7.98 (m, 1H), 8.44 (m, 1H), 8.76 (m, 1H), 9.15 (s, 1H).

Provenance & Evidence