Carbon tetrabromide → HCID 57537543, compound

Participants

Reaction Conditions

Reaction Steps

4-Trifluoromethyl-1-triisopropylsilanyl-1H-pyrrolo[2,3-b]pyridine (1.54 g, 4.5 mmol) was dissolved in tetrahydrofuran (50 mL) and cooled to −78° C. Sec-butyllithium (1.4 M in cyclohexane, 10 mL, 14 mmol) was added dropwise and the mixture was stirred at −78° C. for 1 h. A solution of carbontetrabromide (4.5 g, 13.5 mmol) in tetrahydrofuran (20 mL) was added quickly at −78° C. and the mixture was stirred for 15 min. The reaction was quenched with saturated ammonium chloride solution. The mixture was warmed to ambient temperature and the layers were separated. The organic layer was dried with magnesium and concentrated. Purification by flash silica gel chromatography using a gradient of (ethyl acetate and methanol 9:1) in hexanes afforded 5-Bromo-4-trifluoromethyl-1H-pyrrolo[2,3-b]pyridine (170 mg, 0.64 mmol, 9% yield). 1H NMR (500 MHz, DMSO-d6) δ 12.49 (bs, 1H), 8.54 (s, 1H), 7.82 (m, 1H), 6.61 (m, 1H). MS: m/z 264.9/266.9 (M+H+).

Provenance & Evidence