Sodium Hydroxide → 5-Chloro-3-methyl-3H-[1,2,3]triazolo[4,5-B]pyridine

Participants

Reaction Conditions

Reaction Steps

NaNO2 (350 mg, 5.08 mmol) was added to a stirred solution of 6-chloro-N2-methylpyridine-2,3-diamine (Step 102.2) (800 mg, 5.08 mmol) in 2N HCl (8 mL) at 0° C. and the resulting mixture was stirred for 10 min at 0° C. The reaction was basified with 2N NaOH and extracted with CH2Cl2. The combined organic layers were washed with brine, dried over Na2SO4, filtered and concentrated under reduced pressure. The crude material was purified by silica gel column chromatography (50% EtOAc/hexane) to afford the title product (545 mg, 3.23 mmol, 64% yield) as beige solid. tR: 0.69 min (LC-MS 2); ESI-MS: 168/170 [M+H]+ (LC-MS 2); Rf=0.46 (50% EtOAc/hexane); 1H NMR (400 MHz, DMSO-d6) δ ppm 4.25 (s, 3H) 7.44-7.62 (m, 1H) 8.62 (d, J=8.6 Hz, 1H).

Provenance & Evidence