5-iodo-N,6-dimethyl-2-oxo-1-[3-(trifluoromethyl)phenyl]-1,2-dihydropyridine-3-carboxamide → 5-[2-(4-Chloro-phenyl)-2H-pyrazol-3-yl]-6-methyl-2-oxo-1-(3-trifluoromethyl-phenyl)-1,2-dihydro-pyridine-3-carboxylic Acid Methylamide

HRID 1672598Notes

Reaction equation

[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]2[C:12]([Sn](CCCC)(CCCC)CCCC)=[CH:11][CH:10]=[N:9]2)=[CH:4][CH:3]=1.[CH3:26][NH:27][C:28]([C:30]1[C:31](=[O:48])[N:32]([C:38]2[CH:43]=[CH:42][CH:41]=[C:40]([C:44]([F:47])([F:46])[F:45])[CH:39]=2)[C:33]([CH3:37])=[C:34](I)[CH:35]=1)=[O:29]>COCCOC>[CH3:26][NH:27][C:28]([C:30]1[C:31](=[O:48])[N:32]([C:38]2[CH:43]=[CH:42][CH:41]=[C:40]([C:44]([F:47])([F:45])[F:46])[CH:39]=2)[C:33]([CH3:37])=[C:34]([C:12]2[N:8]([C:5]3[CH:4]=[CH:3][C:2]([Cl:1])=[CH:7][CH:6]=3)[N:9]=[CH:10][CH:11]=2)[CH:35]=1)=[O:29]

Participants

Conditions

Temperature: 100 °C

Procedure

1-(4-Chloro-phenyl)-5-tributylstannanyl-1H-pyrazole (0.107 g, 0.22 mmol), 5-iodo-6-methyl-2-oxo-1-(3-trifluoromethyl-phenyl)-1,2-dihydro-pyridine-3-carboxylic acid methylamide (0.05 g, 0.11 mmol), Pd(PBut3)2 (10 mg) and DME (2 ml) were placed in a tube for microwave synthesis. The mixture was degassed with argon and heated in a synthesis microwave heater (CEM) at 100° C. (max 150 W) for 10 minutes. The solvent was removed in vacuo giving a crude product which was purified on silica and then further purified on preparative HPLC. The pure fractions were freeze-dried giving 10 mg (17%) of the title compound.

Workup

customThe mixture was degassed with argon
customThe solvent was removed in vacuo
customgiving a crude product which
customwas purified on silica
customfurther purified on preparative HPLC
customThe pure fractions were freeze-dried

Sources & evidence

ORD record: ord-f27c7b967f5b4dd0be9da764902e50ae
Source dataset: uspto-grants-2011_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07998984B2

Reaction notes

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