Chloroacetaldehyde → HCID 21866982, compound

Participants

Reaction Conditions

Reaction Steps

Chloroacetaldehyde (12 μL, 0.188 mmol) was added to a mixture of 6-amino-4-(4-bromo-2-chlorophenylamino)-nicotinic acid tert-butyl ester (42) (50 mg, 0.125 mmol) in EtOH (630 μL). After stirring the reaction mixture at 80° C. for 5 hours, an additional 12 μL of chloroacetaldehyde were added and heating was continued for 10 hours. The reaction mixture was cooled to room temperature and diluted with EtOAc to give a cloudy semi-solution. The organic layer was washed with water, saturated NaHCO3 and brine. The organic layer contains a precipitate, which was collected by filtration to give the desired product (43) (15 mg, 33%). MS APCI (−) m/z 364, 366, (M−, Cl, Br pattern) detected. 1H NMR (400 MHz, DMSO-d6) δ 9.12 (s, 1H), 8.31 (s, 1H), 7.91 (s, 1H), 7.80 (s, 1H), 7.65–7.54 (m, 2H), 6.91 (s, 1H).

Provenance & Evidence