Sodium Hydroxide → HCID 59200040, compound

Participants

Reaction Steps

A solution of 2-{5-fluoro-1-[(4-methyl-2-pyridin-2-yl-pyrimidine-5-carbonyl)-amino]-1H-indol-3-yl}-2-methyl-propionic acid methyl ester (0.85 mmol) in MeOH (5 mL) is treated with 10% aqueous NaOH (2 mL) and stirred at rt overnight. The mixture is then concentrated, diluted with EtOAc (50 mL), and extracted with 10% aqueous NaOH (3×50 mL). The aqueous layer is acidified with 12 M aqueous HCl, extracted with DCM (3×50 mL). The combined organic layer is dried (Na2SO4), filtered and concentrated. The residue is triturated with Et2O to afford 2-[5-fluoro-1-[(4-methyl-2-pyridin-2-yl-pyrimidine-5-carbonyl)-amino]-1H-indol-3-yl]-2-methyl-propionic acid (100 mg, 27%, 3 steps). MS: 434 (M+H); 1H NMR (300 MHz, DMSO-d6): δ 9.26 (s, 1H), 8.79 (m, 1H), 8.44 (d, 1H), 8.03 (t, 1H), 7.59 (m, 1H), 7.53 (s, 1H), 7.49 (m, 1H), 7.35 (d, 1H), 7.08 (t, 1H), 2.79 (s, 3H), 1.59 (s, 6H).

Provenance & Evidence