Ammonium Chloride → HCID 86634761, compound

Participants

Reaction Conditions

Reaction Steps

A flask was charged with (3-(dimethylamino)propyl)triphenylphosphonium bromide (0.555 g, 1.30 mmol) and THF (5 mL) and cooled to 0° C. Butyllithium (0.518 mL, 1.30 mmol) was added. The reaction was stirred at 0° C. for 20 minutes, and then 4-(2,6-difluorophenoxy)-6-(4-methylthiazol-2-ylamino)nicotinaldehyde (Example 146; 0.150 g, 0.432 mmol) was added. The reaction was stirred at ambient temperature overnight. Water and saturated NH4Cl were added, and the reaction was extracted with ethyl acetate and dichloromethane. The organic layer was dried, filtered and concentrated, and the crude material was purified by silica gel column chromatography eluting with DCM-2-5% methanol/DCM. The isolated material was treated with 2M HCl in ether and dried over high vacuum to give the title compound (0.165 mg, 78% yield) as a white solid. 1H NMR (CDCl3) δ 8.43 (s, 0.5H), 8.22 (s, 0.5H), 7.29 (m, 1H), 7.25 (m, 1H), 7.08 (m, 2H), 6.95 (d, 0.5H), 6.68 (d, 0.5H), 6.38 (d, 1H), 6.31 (d, 1H), 3.16 (dt, 2H), 2.87 (s, 6H), 2.79 (m, 2H), 2.32 (d, 3H).

Provenance & Evidence