Sodium Azide → HCID 86596995, compound

Participants

Reaction Conditions

Reaction Steps

4,6-Dichloro-5-methyl-nicotinic acid (J. Heterocyclic Chemistry 1999, 36, 953–957) was converted to 7-(4-bromo-2-chloro-phenylamino)-8-methyl-imidazo[1,2-a]pyridine-6-carboxylic acid according to the steps described in the alternate synthesis of Step D, Example 9. It was determined that addition of sodium azide to the 4-(4-bromo-2-chloro-phenylamino)-6-chloro-5-methyl-nicotinic acid methyl ester intermediate required heating to 50° C., which results in a separable mixture of the desired methyl ester, 6-azido-4-(4-bromo-2-chloro-phenylamino)-5-methyl-nicotinic acid methyl ester, and the corresponding carboxylic acid. MS ESI (+) m/z 380, 382 (M+, Cl, Br pattern) detected. 1H NMR (400 MHz, DMSO-d6) δ 9.46 (s, 1H), 9.40 (br s, 1H), 8.25 (d, 1H), 8.12 (d, 1H), 7.79 (m, 1H), 7.42 (dd, 1H), 6.80 (d, 1H), 2.07 (s, 3H).

Provenance & Evidence