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

HRID 17310Notes

Reaction equation

C(=O)([O-])[O-].[K+].[K+].[CH2:7]([O:14][C:15]1[CH:16]=[C:17]([C:21]2[C:26]([CH3:27])=[C:25]([C:28]#[N:29])[C:24]([NH:30]C(=O)C(F)(F)F)=[C:23]([O:37][CH3:38])[C:22]=2[F:39])[CH:18]=[CH:19][CH:20]=1)[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1>CO>[NH2:30][C:24]1[C:23]([O:37][CH3:38])=[C:22]([F:39])[C:21]([C:17]2[CH:18]=[CH:19][CH:20]=[C:15]([O:14][CH2:7][C:8]3[CH:9]=[CH:10][CH:11]=[CH:12][CH:13]=3)[CH:16]=2)=[C:26]([CH3:27])[C:25]=1[C:28]#[N:29]

Participants

Conditions

Temperature: 70 °C

Procedure

Aqueous potassium carbonate solution (20% w/v, 6.07 ml), methanol (12.1 ml) were added to N-(3′-benzyloxy-5-cyano-2-fluoro-3-methoxy-6-methylbiphenyl-4-yl)-2,2,2-trifluoroacetamide (I-53) (400 mg, 873 μmol), followed by stirring overnight at 70° C. After cooling, methanol was evaporated away under reduced pressure, saturated brine (50 ml) was added, the product was extracted with ethyl acetate (50 ml×2). The organic layer was dried over anhydrous magnesium sulfate, concentrated under reduced pressure. The residue was purified by silica gel column chromatography (n-hexane:ethyl acetate=4:1) to obtain the entitled compound (276 mg, 87%) as a colorless solid.

Workup

temperatureAfter cooling
custommethanol was evaporated away under reduced pressure, saturated brine (50 ml)
additionwas added
extractionthe product was extracted with ethyl acetate (50 ml×2)
dry with materialThe organic layer was dried over anhydrous magnesium sulfate
concentrationconcentrated under reduced pressure
customThe residue was purified by silica gel column chromatography (n-hexane:ethyl acetate=4:1)

Sources & evidence

ORD record: ord-01c534719cee4fdba2975acbe1d88c34
Source dataset: uspto-grants-2010_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07737166B2

Reaction notes

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