2,3-Dichloro-5,6-dicyano-1,4-benzoquinone → 4-Methyl-2-pyridin-2-yl-pyrimidine-5-carboxylic acid (5-fluoro-3-formyl-indol-1-yl)-amide

Participants

Reaction Steps

A solution of 4-methyl-2-pyridin-2-yl-pyrimidine-5-carboxylic acid (5-fluoro-indol-1-yl)-amide (250 mg, 0.55 mmol) in H2O (5.5 mL) is treated with DDQ (369 mg, 1.6 mmol) in EtOAc (0.5 mL), and stirred at rt for 2 h. The mixture is diluted with EtOAc (50 mL), washed with brine (50 mL), and extracted with saturated aqueous NaHCO3 (3×50 mL). The aqueous layer is acidified to pH 2 with HCl (conc.) and washed with Et2O (50 mL). The aqueous layer is neutralized with 10% aqueous NaOH and extracted with EtOAc (3×50 mL). The combined organic layer is dried (Na2SO4), filtered and concentrated in vacuo. The residue is purified by triturating in Et2O to afford 4-methyl-2-pyridin-2-yl-pyrimidine-5-carboxylic acid (5-fluoro-3-formyl-indol-1-yl)-amide (87 mg, 43%). MS: 376 (M+H); 1H NMR (300 MHz, DMSO-d6): δ 12.53 (s, NH, 1H), 10.00 (s, 1H), 9.34 (m, 1H), 8.81 (m, 1H), 8.66 (s, 1H), 8.48 (m, 1H), 8.04 (m, 1H), 7.86 (m, 1H), 7.72 (m, 1H), 7.61 (m, 1H), 7.27 (m, 1H), 2.80 (s, 3H).

Provenance & Evidence