Water → HCID 18782485, compound

HRID 1420689Notes

Reaction equation

[H-].[Na+].[Br:3][C:4]1[CH:9]=[C:8]([NH:10][C:11](=[O:16])[C:12]([F:15])([F:14])[F:13])[CH:7]=[CH:6][C:5]=1[O:17][CH3:18].[CH3:19]I.O>CN(C)C=O>[Br:3][C:4]1[CH:9]=[C:8]([N:10]([CH3:19])[C:11](=[O:16])[C:12]([F:14])([F:13])[F:15])[CH:7]=[CH:6][C:5]=1[O:17][CH3:18]

Participants

Conditions

Temperature: 0 °C

Procedure

Sodium hydride (60% dispersion in mineral oil, 0.48 g, 12 mmol) was added to a stirred, cooled (0° C.) solution of 2-bromo-4-(trifluoroacetamido)anisole (Description 4(b); 2.98 g, 10 mmol) in dimethylformamide (30 ml). The mixture was stirred at 0° C. for 30 minutes, then methyl iodide (0.75 ml, 1.70 g, 12 mmol) was added. The mixture was stirred at 0° C. for 30 minutes, then at room temperature for 3 hours. Water (50 ml) was added and the mixture was extracted with ethyl acetate (3×50 ml). The combined organic extracts were washed with water (4×50 ml) then brine (50 ml), dried (MgSO4) and the solvent evaporated under reduced pressure. The residue was purified by flash chromatography, eluting with hexane/CH2Cl2 (50:50 increasing to 30:70), to give the title compound as a colorless solid (2.72 g, 87%); δH (250MHz, CDCl3) 3.32 (3H, s, N--CH3), 3.94 (3H, s, ArOCH3), 6.91 (1H, d, J 8.7Hz, 6-H), 7.18 (1H, dd, J 8.7, 2.4Hz, 5-H), 7.46 (1H, d, J 2.4Hz, 3-H).

Workup

stirringThe mixture was stirred at 0° C. for 30 minutes
waitat room temperature for 3 hours
extractionthe mixture was extracted with ethyl acetate (3×50 ml)
washThe combined organic extracts were washed with water (4×50 ml)
dry with materialbrine (50 ml), dried (MgSO4)
customthe solvent evaporated under reduced pressure
customThe residue was purified by flash chromatography
washeluting with hexane/CH2Cl2 (50:50 increasing to 30:70)

Sources & evidence

ORD record: ord-96c7212f7a5c445583f16cc53d842155
Source dataset: uspto-grants-2000_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06071928

Reaction notes

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