Toluene → HCID 66995294, compound

HRID 1160824Notes

Reaction equation

[C:1]1(C)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[C:8]([C:10]1[CH:11]=[C:12]([C:24]2[CH:25]=[C:26]([CH:31]=[CH:32][N:33]=2)[C:27]([O:29][CH3:30])=[O:28])[CH:13]=[CH:14][C:15]=1OS(C(F)(F)F)(=O)=O)#[N:9].C1(B(O)O)C=CC=CC=1.C(=O)([O-])[O-].[K+].[K+]>C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.O>[C:8]([C:10]1[CH:11]=[C:12]([C:24]2[CH:25]=[C:26]([CH:31]=[CH:32][N:33]=2)[C:27]([O:29][CH3:30])=[O:28])[CH:13]=[CH:14][C:15]=1[C:1]1[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1)#[N:9]

Participants

Conditions

Temperature: 100 °C

Procedure

87 mg of tetrakis(triphenylphosphine)palladium was added to a toluene (25 ml) suspension of 966 mg of methyl 2-(3-cyano-4-{[(trifluoromethyl)sulfonyl]oxy}phenyl)isonicotinate, 610 mg of phenylboronic acid and 518 mg of potassium carbonate, followed by heating at 100° C. in an argon atmosphere for 2 hours. Water was added to the reaction mixture, followed by extraction with ethyl acetate. The organic layer was washed with brine, dried and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (hexane:ethyl acetate=95:5 to 70:30) to obtain 758 mg of methyl 2-(2-cyanobiphenyl-4-yl)isonicotinate.

Workup

extractionfollowed by extraction with ethyl acetate
washThe organic layer was washed with brine
customdried
concentrationconcentrated under reduced pressure
customThe residue was purified by silica gel column chromatography (hexane:ethyl acetate=95:5 to 70:30)

Sources & evidence

ORD record: ord-c4630410c2c04a68898832d4e148cbf2
Source dataset: uspto-grants-2010_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07816558B2

Reaction notes

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