Dimethylformamide → HCID 59513774, compound

Participants

Reaction Steps

A mixture of (2E)-1-[2-(3-bromophenyl)-7-chloropyrazolo[1,5-a]pyridin-3-yl]-3-(dimethylamino)-2-propen-1-one (500 mg, 1.23 mmol—prepared according to WO 02072581 example 1, p. 77) and N-(3-fluorophenyl)urea nitrate (600 mg, 2.8 mmol) were stirred with K2CO3 (1 g, 6.9 mmol) and DMF (5 mL) at 100° C. for 15 h. The reaction was then stirred at rt for 7 days. The resulting brown solution was concentrated under vacuum, partitioned between EtOAc and water. The organic fraction was washed with brine and dried over MgSO4. The crude solution was concentrated and purified by silica gel column chromatography (20-100% gradient EtOAc/hexanes). The purification yielded 254 mg (42%) of an orange powder. ESIMS (M+H)+=505.13

Provenance & Evidence