Hydrochloric Acid → HCID 57517571, compound

To a solution of 2-(5-bromopyridin-2-yl)-2-methylpropanenitrile (2.0 g, 8.9 mmol) in dichloromethane (20 mL) under nitrogen was added DIBAL-H (12.4 mL, 12.4 mmol, 1.0 M in THF) dropwise at −30° C. The resulting solution was stirred at ambient temperature for 3 hours before the addition of 2 N aqueous HCl (10 mL) at 0° C. The resulting solution was stirred at ambient temperature for 10 minutes, the solution was basified with saturated aqueous NaHCO3 to pH 8-9, and then extracted with EtOAc (3×20 mL). The combined organic layers were dried over sodium sulfate, filtered and concentrated in vacuo. The crude residue was purified by MPLC on Silica gel (eluting with 2-4% EtOAc/hexane) to afford the title compound as a yellow oil. 1H NMR (300 MHz, CDCl3) δ 9.73 (s, 1H), 8.66 (s, 1H), 7.82 (d, J=8.7 Hz, 1H), 7.17 (d, J=8.7 Hz, 1H), 1.47 (s, 6H). MS ESI: [M+H]+ m/z 228, 230.

1. extractionextracted with EtOAc (3×20 mL)
2. dry with materialThe combined organic layers were dried over sodium sulfate
3. filtrationfiltered
4. concentrationconcentrated in vacuo
5. customThe crude residue was purified by MPLC on Silica gel (eluting with 2-4% EtOAc/hexane)

ORD record

ord-24c43e4f8f2d4c7bbd0a94a0198ee0d0

Source dataset

uspto-grants-2015_02

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08962608B2