Dimethylformamide → N-(3-bromo-6-cyano-2-methoxy-5-methyl-4-styrylphenyl)-2,2-dimethylpropionamide

HRID 17271Notes

Reaction equation

CN(C)C=O.[Br:6][C:7]1[C:8]([O:24][CH3:25])=[C:9]([NH:17][C:18](=[O:23])[C:19]([CH3:22])([CH3:21])[CH3:20])[C:10]([C:15]#[N:16])=[C:11]([CH3:14])[C:12]=1I.[CH:26](/B(O)O)=[CH:27]\[C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1>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(OCC)(=O)C>[Br:6][C:7]1[C:8]([O:24][CH3:25])=[C:9]([NH:17][C:18](=[O:23])[C:19]([CH3:22])([CH3:21])[CH3:20])[C:10]([C:15]#[N:16])=[C:11]([CH3:14])[C:12]=1[CH:26]=[CH:27][C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1

Participants

Conditions

Temperature: 95 °C

Procedure

Tetrakis(triphenylphosphine)palladium(0) (6.4 mg, 5.5 μmol) was added to an N,N-dimethylformamide (1.0 ml) suspension of N-(3-bromo-6-cyano-4-iodo-2-methoxy-5-methylphenyl)-2,2-dimethylpropionamide (I-6) (50 mg, 111 μmol), trans-β-styreneboronic acid (17.2 mg, 116 μmol), potassium phosphate n-hydrate (74-78%, 64 mg, 222 μmol), followed by stirred overnight at 95° C. The reaction liquid was cooled, then ethyl acetate (30 ml) was added, followed by washing with saturated brine (30 ml×2), drying over anhydrous magnesium sulfate, concentrating under reduced pressure.

Workup

customThe reaction liquid
temperaturewas cooled
washby washing with saturated brine (30 ml×2)
dry with materialdrying over anhydrous magnesium sulfate
concentrationconcentrating under reduced pressure

Sources & evidence

ORD record: ord-be1549dc55c14a9f9e3975d546dc35d8
Source dataset: uspto-grants-2010_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07737166B2

Reaction notes

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