Tri(butyl)vinyltin → 4'-Trifluoromethylbiphenyl-2-carboxylic acid (2-dimethylcarbamoyl-4-vinylphenyl)amide

HRID 423276Notes

Reaction equation

[CH3:1][N:2]([CH3:31])[C:3]([C:5]1[CH:10]=[C:9](I)[CH:8]=[CH:7][C:6]=1[NH:12][C:13]([C:15]1[C:16]([C:21]2[CH:26]=[CH:25][C:24]([C:27]([F:30])([F:29])[F:28])=[CH:23][CH:22]=2)=[CH:17][CH:18]=[CH:19][CH:20]=1)=[O:14])=[O:4].[CH2:32](C([Sn])=C(CCCC)CCCC)[CH2:33]CC>C1(C)C=CC=CC=1>[CH3:1][N:2]([CH3:31])[C:3]([C:5]1[CH:10]=[C:9]([CH:32]=[CH2:33])[CH:8]=[CH:7][C:6]=1[NH:12][C:13]([C:15]1[C:16]([C:21]2[CH:26]=[CH:25][C:24]([C:27]([F:30])([F:29])[F:28])=[CH:23][CH:22]=2)=[CH:17][CH:18]=[CH:19][CH:20]=1)=[O:14])=[O:4]

Participants

Conditions

Temperature: 140 °C

Procedure

To a solution of 4′-trifluoromethylbiphenyl-2-carboxylic acid (2-dimethylcarbamoyl-4-iodophenyl)amide (1.32 g) in toluene (15 mL) were added tributylvinyltin (935 mg) and tetrakistriphenylphosphine palladium(0) (142 mg), and the mixture was stirred at 140° C. for 1.5 hours under heating. The reaction solution was allowed to stand for cooling down to room temperature, and concentrated in vacuo. The residue was purified by column chromatography on silica gel (hexane:ethyl acetate=2:1, v/v) to give the title compound (783 mg).

Workup

temperatureunder heating
temperaturefor cooling down to room temperature
concentrationconcentrated in vacuo
customThe residue was purified by column chromatography on silica gel (hexane

Sources & evidence

ORD record: ord-95742c28dfbc4d9abb2f2653b3108f4f
Source dataset: uspto-grants-2012_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08101774B2

Reaction notes

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