Potassium Carbonate → 4-Amino-6-bromo-5-methoxy-2-methylbiphenyl-3-carbonitrile

HRID 17297Notes

Reaction equation

C(=O)([O-])[O-].[K+].[K+].[Br:7][C:8]1[C:13]([O:14][CH3:15])=[C:12]([NH:16]C(=O)C(F)(F)F)[C:11]([C:23]#[N:24])=[C:10]([CH3:25])[C:9]=1[C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1>CO>[NH2:16][C:12]1[C:13]([O:14][CH3:15])=[C:8]([Br:7])[C:9]([C:26]2[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=2)=[C:10]([CH3:25])[C:11]=1[C:23]#[N:24]

Participants

Conditions

Temperature: 70 °C

Procedure

Aqueous potassium carbonate solution (1.25 ml) [potassium carbonate (15 g) was dissolved in water (100 ml)] and methanol (1.25 ml) were added to N-(2-bromo-5-cyano-3-methoxy-6-methylbiphenyl-4-yl)2,2,2-trifluoroacetamide (I-38) (133 mg, 0.322 mmol), followed by stirring overnight at 70° C. After cooling, methanol was evaporated away under reduced pressure, followed by extraction with ethyl acetate, washing with saturated brine and drying on anhydrous magnesium sulfate, the solvent was concentrated under reduced pressure to obtain a pale brown residue. The resulting residue was purified by silica gel column chromatography (n-hexane:ethyl acetate=6:1) to obtain the entitled compound (95 mg, 94%) as a colorless solid.

Workup

temperatureAfter cooling
custommethanol was evaporated away under reduced pressure
extractionfollowed by extraction with ethyl acetate
washwashing with saturated brine
dry with materialdrying on anhydrous magnesium sulfate
concentrationthe solvent was concentrated under reduced pressure
customto obtain a pale brown residue
customThe resulting residue was purified by silica gel column chromatography (n-hexane:ethyl acetate=6:1)

Sources & evidence

ORD record: ord-9aa13dd326e54abfb0181b08fd8f4200
Source dataset: uspto-grants-2010_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07737166B2

Reaction notes

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