Water → HCID 71812191, compound

Participants

Reaction Conditions

Reaction Steps

Into a suspension of 4-chloro-3-nitro-1H-pyrrolo[2,3-b]pyridine (50.0 g) in acetic acid (300 mL) were added N-bromosuccinimide (NBS, 70.9 g, 1.60 equiv) in small portions at 25° C. The reaction mixture was stirred at 25° C. for 18 h. Water (3.0 mL) was added slowly over 30 min to get a light yellow slurry. The resulting solid was collected by filtration and washed with a 2:2:1 (v/v/v) mixture of saturated sodium sulfite solution, water, and methanol, followed by water and a 1:1 (v/v) mixture of methanol and water. The cake was dried in a vacuum at 50° C. oven overnight to give the 44.9 g (65% yield) of 5-bromo-4-chloro-3-nitro-1H-pyrrolo[2,3-b]pyridine as an light yellow solid. 1H NMR (300 MHz, DMSO-d6) δ 13.7 (s, 1H), 8.93 (s, 1H), 8.66 (s, 1H). 13C NMR (75 MHz, DMSO-d6) δ 146.9, 146.4, 133.9, 133.2, 127.0, 116.7, 111.3. HRMS calcd. For C7H2BrC1N3O2 [M-H]−: 273.9024, found 273.9031.

Provenance & Evidence