HCID 58092073, compound → Benzamide
Reaction equation
Br[C:2]1[CH:3]=[C:4]([CH:13]=[CH:14][C:15]=1F)[C:5]([NH:7]C[Si](C)(C)C)=[O:6]>CN(C=O)C.C(OCC)(=O)C.[C-]#N.[Zn+2].[C-]#N.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[C:5]([NH2:7])(=[O:6])[C:4]1[CH:13]=[CH:14][CH:15]=[CH:2][CH:3]=1Participants
6
Conditions
- Temperature
- 90 °C
Procedure
3-bromo-4-fluoro-N-[(trimethylsilyl)methyl]benzamide (5.0 g) was dissolved in DMF, and zinc cyanide (1.4 g) and tetrakis(triphenylphosphine)palladium (1.9 g) were added thereto under argon atmosphere. The reaction mixture was stirred for 4 hours at 90° C. The reaction mixture was returned to room temperature. The mixture was diluted with ethyl acetate and washed with a saturated aqueous sodium hydrogen carbonate solution, subsequently dried over magnesium sulfate. After filtering the reaction mixture, the solvent was distilled off under reduced pressure, and the resulting mixture was purified by silica gel chromatography, to obtain 3-cyano-4-fluoro-N-[trimethylsilyl)methyl]benzamide (4.0 g) at a yield of 97%.
Workup
- customwas returned to room temperature
- washwashed with a saturated aqueous sodium hydrogen carbonate solution
- dry with materialsubsequently dried over magnesium sulfate
- filtrationAfter filtering the reaction mixture
- distillationthe solvent was distilled off under reduced pressure
- customthe resulting mixture was purified by silica gel chromatography
Sources & evidence
- ORD record
- ord-97b92e1587924208a15e34db39b0a635
- Source dataset
- uspto-grants-2012_11
- Patent number
- US08304371B2
Reaction notes
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