Carbon tetrabromide → HCID 57537543, compound

Temperature

-78 °C

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+).

1. stirringthe mixture was stirred for 15 min
2. customThe reaction was quenched with saturated ammonium chloride solution
3. temperatureThe mixture was warmed to ambient temperature
4. customthe layers were separated
5. dry with materialThe organic layer was dried with magnesium
6. concentrationconcentrated
7. customPurification by flash silica gel chromatography

ORD record

ord-574c9db06e47400eb5d157899ad6555a

Source dataset

uspto-grants-2012_04

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08158647B2