Dimethylformamide → HCID 86614012, compound

Temperature

25 °C

Oxalyl chloride (2.0 M in dichloromethane, 2.08 mL, 4.16 mmol) was added to a suspension of (E)-3-(2-bromo-5-fluorophenyl)acrylic acid (678 mg, 2.77 mmol) in dichloromethane (8 mL). N,N-dimethylformamide (11 □L, 0.14 mmol) was added, and the resulting mixture was stirred at 25° C. for 1 h. The reaction mixture was concentrated in vacuo, and 4-dimethylaminopyridine (3 mg, 0.025 mmol), N,O-dimethylhydroxylamine hydrochloride (270 mg, 2.77 mmol), Hunig's base (1.44 mL, 8.28 mmol), and dichloromethane (8 ml) were added. The mixture was stirred at 25° C. for 10 h, then transferred to a separatory funnel with dichloromethane (100 mL), and the organic layer was extracted sequentially with water (7 mL), 0.5 M sodium carbonate (7 mL), 1 M hydrochloric acid (7 mL), and half-saturated brine (7 mL), and then dried over sodium sulfate and concentrated. Purification of the concentrate by flash column chromatography (33% to 40% EtOAc/hexane) afforded the title compound as a white solid. MS m/z: 288 & 290 (M+1).

1. additionwere added
2. stirringThe mixture was stirred at 25° C. for 10 h
3. extractionthe organic layer was extracted sequentially with water (7 mL), 0.5 M sodium carbonate (7 mL), 1 M hydrochloric acid (7 mL), and half-saturated brine (7 mL)
4. dry with materialdried over sodium sulfate
5. concentrationconcentrated
6. customPurification of the
7. concentrationconcentrate by flash column chromatography (33% to 40% EtOAc/hexane)

ORD record

ord-140e6c7c0d4544e28bf393e04b4d44ab

Source dataset

uspto-grants-2011_01

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07872009B2