Dimethylformamide → HCID 57978836, compound
Reaction equation
[C:1]([C:4]1[CH:9]=[C:8]([CH3:10])[C:7](OS(C(F)(F)F)(=O)=O)=[C:6]([CH3:19])[CH:5]=1)(=[O:3])[NH2:2].C1C=CC(P(C2C=CC=CC=2)CCCP(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.C([SiH](CC)CC)C.CN([CH:59]=[O:60])C>CC([O-])=O.CC([O-])=O.[Pd+2]>[CH:59]([C:7]1[C:8]([CH3:10])=[CH:9][C:4]([C:1]([NH2:2])=[O:3])=[CH:5][C:6]=1[CH3:19])=[O:60]Participants
6
Reactant 4
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 75 °C
Procedure
Into a solution of trifluoro-methanesulfonic acid 4-carbamoyl-2,6-dimethyl-phenyl ester (1.49 g, 5 mmol), Pd(OAc)2 (0.037 g, 0.15 mmol), DPPP (0.062 g, 0.15 mmol) and TEA (1.74 mL, 12.5 mmol) in DMF (25 mL) was bubbled CO (gas) for 10 min, then triethylsilane (1.6 mL, 10 mmol) was added. The resulting mixture was stirred at 75° C. under a CO gas balloon for 6.5 hr. After cooling to room teperature, the reaction was quenched by addition of water, then extracted with EtOAc. The EtOAc extracts were washed with water, brine and then dried over MgSO4. After filtration and evaporation, the residue was purified by column chromatograpghy (eluent, EtOAc-hexanes˜1:1) to yield 4-formyl-3,5-dimethyl-benzamide (11c) as a yellowish solid.
Workup
- temperatureAfter cooling to room teperature
- customthe reaction was quenched by addition of water
- extractionextracted with EtOAc
- washThe EtOAc extracts were washed with water, brine
- dry with materialdried over MgSO4
- filtrationAfter filtration and evaporation
- customthe residue was purified by column chromatograpghy (eluent, EtOAc-hexanes˜1:1)
Sources & evidence
- ORD record
- ord-0148a805c79a43939d98b88bf3ed7cd4
- Source dataset
- uspto-grants-2009_12
- Patent number
- US07629488B2
Reaction notes
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