Potassium Carbonate → 5-Amino-6-fluoro-4-methoxybiphenyl-3-carbonitrile

HRID 17523Notes

Reaction equation

[C:1]([C:3]1[C:4]([O:23][CH3:24])=[C:5]([NH:16]C(=O)C(F)(F)F)[C:6]([F:15])=[C:7]([C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=2)[CH:8]=1)#[N:2].C(=O)([O-])[O-].[K+].[K+]>CO>[NH2:16][C:5]1[C:4]([O:23][CH3:24])=[C:3]([C:1]#[N:2])[CH:8]=[C:7]([C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=2)[C:6]=1[F:15]

Participants

Conditions

Temperature: 70 °C

Procedure

N-(5-Cyano-2-fluoro-4-methoxybiphenyl-3-yl)-2,2,2-trifluoroacetamide 233) (2.78 g, 8.22 mmol) was dissolved in methanol (31.8 ml), and at room temperature, aqueous 15 wt. % potassium carbonate solution (31.8 ml, 34.5 mmol) was added. This was stirred at 70° C. for 38 hours. After cooling to room temperature, methanol was evaporated away under reduced pressure, and the resulting residue was extracted with ethyl acetate. The organic layer was separated, and the aqueous layer was again extracted with ethyl acetate. The organic layers were combined, washed with saturated brine, and dried over anhydrous sodium sulfate. The solvent was evaporated away, and the resulting residue was purified by middle-pressure liquid chromatography (eluent, hexane:ethyl acetate=4:1) to obtain the entitled compound (1.833 g, 92%) as a colorless gel substance.

Workup

temperatureAfter cooling to room temperature
custommethanol was evaporated away under reduced pressure
extractionthe resulting residue was extracted with ethyl acetate
customThe organic layer was separated
extractionthe aqueous layer was again extracted with ethyl acetate
washwashed with saturated brine
dry with materialdried over anhydrous sodium sulfate
customThe solvent was evaporated away
customthe resulting residue was purified by middle-pressure liquid chromatography (eluent, hexane:ethyl acetate=4:1)

Sources & evidence

ORD record: ord-c4ce93116b6449c082c153d16600562f
Source dataset: uspto-grants-2010_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07737166B2

Reaction notes

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