Dimethylformamide → HCID 57898918, compound

Participants

Reaction Conditions

Reaction Steps

N-(5-bromo-4-(2,6-difluorophenoxy)pyridin-2-yl)-4-methylthiazol-2-amine (1.06 g, 2.66 mmol) is dissolved in THF (30 mL) and cooled to −78° C. MeLi (2.07 mL, 3.32 mmol) is added slowly, and stir for 10 minutes. n-Butyllithium (1.33 mL, 3.32 mmol) is added and the reaction mixture is stirred for 15 minutes. DMF (0.413 mL, 5.32 mmol) is added, and the reaction mixture is stirred for 30 minutes. The reaction mixture is warmed to room temperature and AcOH (2 mL) is added. The reaction mixture is stirred at room temperature for 1 hour, poured into saturated aqueous sodium bicarbonate and extracted with ethyl acetate. The combined organic layers are dried over sodium sulfate, filtered and concentrated in vacuo. The residue is purified by silica gel (10-20% EtOAc in hexanes) to afford 4-(2,6-difluorophenoxy)-6-(4-methylthiazol-2-ylamino)nicotinaldehyde.

Provenance & Evidence