Potassium Fluoride → HCID 86665195, compound
Reaction equation
Br[C:2]1[CH:3]=[C:4]([N+:15]([O-:17])=[O:16])[C:5](=[O:14])[N:6]([CH2:9][C:10]([F:13])([F:12])[F:11])[C:7]=1[CH3:8].[F:18][C:19]1[C:24]([CH3:25])=[CH:23][CH:22]=[CH:21][C:20]=1B(O)O.[F-].[K+]>C1COCC1.[Pd].C(P(C(C)(C)C)C(C)(C)C)(C)(C)C.C(P(C(C)(C)C)C(C)(C)C)(C)(C)C>[F:18][C:19]1[C:24]([CH3:25])=[CH:23][CH:22]=[CH:21][C:20]=1[C:2]1[CH:3]=[C:4]([N+:15]([O-:17])=[O:16])[C:5](=[O:14])[N:6]([CH2:9][C:10]([F:13])([F:12])[F:11])[C:7]=1[CH3:8]Participants
6
Conditions
- Temperature
- 66 °C
Procedure
A deoxygenated mixture of 5-bromo-6-methyl-3-nitro-1-(2,2,2-trifluoroethyl)pyridin-2(1H)-one (2.00 g, 6.35 mmol), (2-fluoro-3-methylphenyl)boronic acid (1.95 g, 12.7 mmol), potassium fluoride (2.43 g, 41.9 mmol), and bis(tri-tert-butylphosphine) palladium(0) (0.333 g, 0.652 mmol) in THF (32 mL) was heated at 66° C. for 30 min. The reaction mixture was allowed to cool to 23° C., then partitioned between water (200 mL) and ethyl acetate (200 mL). The organic layer was washed with brine, dried over sodium sulfate and concentrated. The residue was purified by flash column chromatography on silica gel, eluting with hexane initially, grading to 50% EtOAc in hexanes to give the title compound. MS: m/z=345.1 (M+1).
Workup
- temperatureto cool to 23° C.
- custompartitioned between water (200 mL) and ethyl acetate (200 mL)
- washThe organic layer was washed with brine
- dry with materialdried over sodium sulfate
- concentrationconcentrated
- customThe residue was purified by flash column chromatography on silica gel
- washeluting with hexane initially
Sources & evidence
- ORD record
- ord-0765911744a943f38cca3328dc04a988
- Source dataset
- uspto-grants-2014_12
- Patent number
- US08912210B2
Reaction notes
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