Chloroacetaldehyde → HCID 21866997, compound

Participants

Reaction Conditions

Reaction Steps

Chloroacetaldehyde (23 μL, 0.360 mmol) was added to a mixture of 6-amino-4-(4-bromo-2-chlorophenylamino)-5-fluoronicotinic acid tert-butyl ester (45) (75 mg, 0.180 mmol) in EtOH (1 mL). After stirring the reaction mixture at 70° C. for 10 hours, an additional 10 μL chloroacetaldehyde was added and heating was continued for 33 hours. The reaction mixture was cooled to room temperature and desired product (46) was collected by filtration. The filtrate was diluted with EtOAc and washed with water, saturated NaHCO3 and brine. The organic layer was dried (Na2SO4) and concentrated to give additional product (46) (51 mg, 74% combined recovery). MS APCI (−) m/z 382, 384, 386 (M−, Cl, Br pattern) detected. 1H NMR (400 MHz, CD3OD) δ 8.86 (s, 1H), 7.85 (s, 1H), 7.53 (s, 2H), 7.32 (d, 1H), 6.82 (t, 1H). 19F NMR (376 MHz, CD3OD) −148.3 (s).

Provenance & Evidence