Bicarbonate Ion → HCID 67155794, compound

Participants

Reaction Conditions

Reaction Steps

5-Nitro-1H-pyrrolo[2,3-b]pyridine (150 mg, 0.92 mmol) was taken up in dry dichloromethane (9 mL) and was chilled to 0° C. Aluminum chloride (613 mg, 4.60 mmol, 5 eq.) was then added, and the mixture was allowed to stir at 0° C. for 15 minutes. 2-Methyl-2-bromopropane (107 μL, 0.919 mmol) was then added, and the mixture was allowed to gradually warm to room temperature over a 16 hour period. The mixture was then poured into cold saturated bicarbonate solution and extracted with dichloromethane (2×). The extracts were dried over sodium sulfate and concentrated. Prep plate purification (2×1.0 mm plates, 3:1 hexane:ethyl acetate) afforded 3-tert-butyl-5-nitro-1H-pyrrolo[2,3-b]pyridine (8.3 mg, 4%) as a solid. 1H NMR (400 MHz, DMSO-d6) δ 12.25 (br s, 1H), 9.07-9.09 (m, 1H), 8.84-8.86 (m, 1H), 7.48 (s, 1H), 1.42 (s, 9H); m/z (APCI-neg) M−1=218.3.

Provenance & Evidence