Methanol → HCID 67304384, compound

1-(4-Fluoro-phenyl)-1H-imidazole-4-carboxylic acid (18 g, 87 mmol) was dissolved in 90 mL dry THF. Borane tetrahydrofuran complex (174 mL, 1M in THF, 174 mmol) was added dropwise. The reaction was refluxed for 2 h and stirred at room temperature overnight. The reaction mixture was cooled to 0° C. and 100 mL methanol were added dropwise. The solvents were evaporated. The residue was taken up in 100 mL 2N HCl and refluxed for 2 h. The reaction mixture was then cooled to 0° C. and 120 mL 2N sodium hydroxide solution were added dropwise. The solid material was filtered off and dried at 50° C. and 15 mbar. The desired compound was obtained as a white solid (13 g, 78%), MS: m/e=193.2 (M+H)+.

1. temperatureThe reaction was refluxed for 2 h
2. temperatureThe reaction mixture was cooled to 0° C.
3. customThe solvents were evaporated
4. temperaturerefluxed for 2 h
5. temperatureThe reaction mixture was then cooled to 0° C.
6. addition120 mL 2N sodium hydroxide solution were added dropwise
7. filtrationThe solid material was filtered off
8. customdried at 50° C.

ORD record

ord-8d50136d1e8c4b729929df50aab34653

Source dataset

uspto-grants-2011_07

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07973165B2