Triphenylphosphine → HCID 66725395, compound

HRID 559796Notes

Reaction equation

I[C:2]1[CH:3]=[C:4]([C:20]([NH:22][CH2:23][C:24]2[CH:29]=[CH:28][C:27]([S:30]([CH3:33])(=[O:32])=[O:31])=[CH:26][CH:25]=2)=[O:21])[C:5](=[O:19])[N:6]([C:9]2[CH:14]=[CH:13][CH:12]=[C:11]([C:15]([F:18])([F:17])[F:16])[CH:10]=2)[C:7]=1[CH3:8].C([Sn](CCCC)(CCCC)[C:39]1[N:44]=[CH:43][CH:42]=[CH:41][N:40]=1)CCC.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>C1(C)C=CC=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd]>[CH3:8][C:7]1[N:6]([C:9]2[CH:14]=[CH:13][CH:12]=[C:11]([C:15]([F:17])([F:18])[F:16])[CH:10]=2)[C:5](=[O:19])[C:4]([C:20]([NH:22][CH2:23][C:24]2[CH:25]=[CH:26][C:27]([S:30]([CH3:33])(=[O:32])=[O:31])=[CH:28][CH:29]=2)=[O:21])=[CH:3][C:2]=1[C:39]1[N:44]=[CH:43][CH:42]=[CH:41][N:40]=1

Participants

Conditions

Temperature: 100 °C

Procedure

Tris(dibenzylideneacetone)-dipalladium(0) (1 mg) was added to 5-iodo-6-methyl-N-[4-(methylsulfonyl)benzyl]-2-oxo-1-[3-(trifluoromethyl)-phenyl]-1,2-dihydropyridine-3-carboxamide (20 mg, 0.034 mmol), 2-(tributyl-stannyl)pyrimidine (25 mg, 0.068 mmol) and triphenylphosphine (1.9 mg, 0.007 mmol) in toluene (1.6 ml) under argon and the mixture was stirred at 100° C. overnight. After cooling, the mixture was filtered through celite and evaporated. The residue was purified by preparative HPLC. Pure fractions were freeze-dried to give the title compound (5 mg, 27%).

Workup

temperatureAfter cooling
filtrationthe mixture was filtered through celite
customevaporated
customThe residue was purified by preparative HPLC
customPure fractions were freeze-dried

Sources & evidence

ORD record: ord-40a2f57138c049d08df16f6c372b2768
Source dataset: uspto-grants-2011_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08063073B2

Reaction notes

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