1221398-11-3

45644-21-1

1221398-11-3

The general procedure for the synthesis of 6-chloro-5-iodopyridin-2-amine from 2-amino-6-chloropyridine was as follows: to a solution of N,N-dimethylformamide (DMF, 700 mL) of 2-amino-6-chloropyridine (50.0 g, 389 mmol) was added N-iodosuccinimide (NIS, 105 g, 467 mmol). The reaction mixture was stirred at room temperature for 12 h. The reaction solution was brown in color. After completion of the reaction, the mixture was poured into water (2.1 L) and the precipitate was collected by filtration. The filter cake was washed with water (2 x 500 mL) and subsequently dried under vacuum. Purification by fast column chromatography (FCC, silica gel; 5-20% ethyl acetate/petroleum ether) gave 6-chloro-5-iodopyridin-2-amine (83 g, 75% yield) as a pink solid. Mass spectrum (ESI): calculated value C5H4ClIN2, 253.9; measured value m/z 254.7 [M + H]+. 1H NMR (400 MHz, CDCl3) δ 7.74 (d, J = 8.0 Hz, 1H), 6.20 (d, J = 8.0 Hz, 1H), 4.69 (br s, 2H).