Carbon tetrabromide → HCID 57537483, compound

Temperature

0 °C

2,2,6,6-Tetramethylpiperidine (380 μL, 2.25 mol) was dissolved in tetrahydrofuran (3 mL) and cooled to 0° C. N-Butyllithium (2.5 M in hexanes, 1.06 mL, 2.66 mmol) was added dropwise and the mixture was stirred at 0° C. for 10 min, then cooled to −78° C. A solution of 1-triisopropylsilanyl-1H-pyrrolo[2,3-b]pyridine-4-carbonitrile (613 mg, 2.04 mmol) in tetrahydrofuran (2 mL) was added at −78° C. and the mixture was stirred at −78° C. for 1 h. A solution of carbontetrabromide (2 g, 6.1 mmol) in tetrahydrofuran (5 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 applied to a Varian chemelut cartridge and eluted with ethyl acetate. The crude product was purified by flash silica gel chromatography using a gradient of dichloromethane in hexanes to afford 5-Bromo-1-triisopropylsilanyl-1H-pyrrolo[2,3-b]pyridine-4-carbonitrile (160 mg, 0.42 mmol, 21% yield). 1H NMR (500 MHz, DMSO-d6) δ 8.57 (s, 1H), 7.88 (d, J=3.5 Hz, 1H), 6.83 (d, J=3.5 Hz, 1H), 1.85 (septet, J=7.5 Hz, 3H), 1.04 (d, J=7.5 Hz, 18H). MS: m/z 378.0/380.0 (M+H+).

1. temperaturecooled to −78° C
2. stirringthe mixture was stirred at −78° C. for 1 h
3. stirringthe mixture was stirred for 15 min
4. customThe reaction was quenched with saturated ammonium chloride solution
5. temperatureThe mixture was warmed to ambient temperature
6. washeluted with ethyl acetate
7. customThe crude product was purified by flash silica gel chromatography

ORD record

ord-d79b3c4c8fa948ee97f9621adc7e5ac4

Source dataset

uspto-grants-2012_04

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08158647B2