Potassium Carbonate → 4-Amino-3-cyano-6-fluoro-5-methoxy-2-methylbiphenyl

HRID 17296Notes

Reaction equation

C(=O)([O-])[O-].[K+].[K+].[C:7]([C:9]1[C:10]([NH:25]C(=O)C(F)(F)F)=[C:11]([O:23][CH3:24])[C:12]([F:22])=[C:13]([C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)[C:14]=1[CH3:15])#[N:8]>CO>[NH2:25][C:10]1[C:11]([O:23][CH3:24])=[C:12]([F:22])[C:13]([C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)=[C:14]([CH3:15])[C:9]=1[C:7]#[N:8]

Participants

Conditions

Temperature: 70 °C

Procedure

Aqueous 20% (w/v) potassium carbonate solution (9.0 ml, 13.0 mmol) was added to a methanol (9 ml) suspension of N-(5-cyano-2-fluoro-3-methoxy-6-methylbiphenyl-4-yl)-2,2,2-trifluoroacetamide (I-37) (400 mg, 1.14 mmol), followed by stirring at 70° C. for 16 hours. The reaction liquid became uniform with temperature elevation. The reaction liquid was cooled to room temperature, methanol was evaporated away under reduced pressure, water was added to the residue, followed by extraction twice with ethyl acetate, the organic layer was washed with saturated brine, then dried over anhydrous magnesium sulfate. After nitration and concentration under reduced pressure, the entitled compound (266 mg, 91%) was obtained as a white solid.

Workup

customThe reaction liquid
customThe reaction liquid
temperaturewas cooled to room temperature
custommethanol was evaporated away under reduced pressure, water
additionwas added to the residue
extractionfollowed by extraction twice with ethyl acetate
washthe organic layer was washed with saturated brine
dry with materialdried over anhydrous magnesium sulfate
concentrationAfter nitration and concentration under reduced pressure

Sources & evidence

ORD record: ord-f4a8f644cd3f4cc0b89eab4ebdd56763
Source dataset: uspto-grants-2010_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07737166B2

Reaction notes

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