Toluene → 6-Methyl-N-[4-(methylsulfonyl)benzyl]-2-oxo-5-phenyl-1-[3-(trifluoromethyl)phenyl]-1,2-dihydropyridine-3-carboxamide

HRID 559789Notes

Reaction equation

[C:1]1(B(O)O)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.I[C:11]1[CH:12]=[C:13]([C:29]([NH:31][CH2:32][C:33]2[CH:38]=[CH:37][C:36]([S:39]([CH3:42])(=[O:41])=[O:40])=[CH:35][CH:34]=2)=[O:30])[C:14](=[O:28])[N:15]([C:18]2[CH:23]=[CH:22][CH:21]=[C:20]([C:24]([F:27])([F:26])[F:25])[CH:19]=2)[C:16]=1[CH3:17].C1(C)C=CC=CC=1.C([O-])([O-])=O.[Na+].[Na+]>C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.Cl[Pd]Cl.[Fe+2].C(O)C>[CH3:17][C:16]1[N:15]([C:18]2[CH:23]=[CH:22][CH:21]=[C:20]([C:24]([F:27])([F:25])[F:26])[CH:19]=2)[C:14](=[O:28])[C:13]([C:29]([NH:31][CH2:32][C:33]2[CH:34]=[CH:35][C:36]([S:39]([CH3:42])(=[O:41])=[O:40])=[CH:37][CH:38]=2)=[O:30])=[CH:12][C:11]=1[C:1]1[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

Conditions

Temperature: 80 °C

Procedure

A mixture of phenylboronic acid (25 mg, 0.20 mmol), 1,1′bis(diphenylphosphino)ferrocenedichloropalladium(II) (4 mg, 0.005 mmol), 5-iodo-6-methyl-N-[4-(methylsulfonyl)benzyl]-2-oxo-1-[3-(trifluoromethyl)phenyl]-1,2-dihydropyridine-3-carboxamide (100 mg 0.17 mmol), toluene (1 ml), ethanol (99%, 0.25 ml) and Na2CO3 (2M, 0.25 ml) was stirred at 80° C. overnight, concentrated and the residue was purified by flash chromatography to give the title compound (70 mg, 76%).

Workup

concentrationconcentrated
customthe residue was purified by flash chromatography

Sources & evidence

ORD record: ord-81f1eef646744551b9e33901497e0f02
Source dataset: uspto-grants-2011_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08063073B2

Reaction notes

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