Dimethylformamide → 6-Phenylnaphthalene-2-carbonitrile

HRID 1594943Notes

Reaction equation

C([O-])([O-])=O.[Cs+].[Cs+].[C:7]1(B(O)O)[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1.C[N:17]([CH:19]=O)C>C([O-])(=O)C.[Pd+2].C([O-])(=O)C>[C:7]1([C:7]2[CH:12]=[C:11]3[C:10](=[CH:9][CH:8]=2)[CH:9]=[C:8]([C:19]#[N:17])[CH:7]=[CH:12]3)[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1

Participants

Conditions

Temperature: 80 °C

Procedure

A solution of Example 121B (300 mg, 1 mmol), palladium (II) acetate (22 mg, 0.1 mmol) and 1-1′-bis(diphenyphosphino)ferrocene (111 mg, 0.2 mmol) was stirred in DMF (3 mL) for 15 minutes, treated with Cs2CO3 (813 mg, 2.5 mmol) and phenylboronic acid (228 mg, 1.5 mmol), stirred for 20 minutes at 80° C., cooled, treated with pH 7 buffer (10 mL), and extracted with diethyl ether. The ether extracts were dried (MgSO4), concentrated, filtered, and purified on silica gel with 10% ethyl acetate/hexane to provide 140 mg of the title compound as a white solid.

Workup

temperaturecooled
additiontreated with pH 7 buffer (10 mL)
extractionextracted with diethyl ether
dry with materialThe ether extracts were dried (MgSO4)
concentrationconcentrated
filtrationfiltered
custompurified on silica gel with 10% ethyl acetate/hexane

Sources & evidence

ORD record: ord-926b033f935e45078a606cefaf98aeec
Source dataset: uspto-grants-2001_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06284796B1

Reaction notes

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