4-(5-Tributylstannanyl-[1,2,3]triazol-1-yl)-benzonitrile → 5-[3-(4-Cyano-phenyl)-3H-[1,2,3]triazol-4-yl]-6-methyl-2-oxo-1-(3-trifluoromethyl-phenyl)-1,2-dihydro-pyridine-3-carboxylic Acid Methylamide

HRID 1672601Notes

Reaction equation

C([Sn](CCCC)(CCCC)[C:6]1[N:10]([C:11]2[CH:18]=[CH:17][C:14]([C:15]#[N:16])=[CH:13][CH:12]=2)[N:9]=[N:8][CH:7]=1)CCC.[CH3:27][NH:28][C:29]([C:31]1[C:32](=[O:49])[N:33]([C:39]2[CH:44]=[CH:43][CH:42]=[C:41]([C:45]([F:48])([F:47])[F:46])[CH:40]=2)[C:34]([CH3:38])=[C:35](I)[CH:36]=1)=[O:30]>COCCOC>[CH3:27][NH:28][C:29]([C:31]1[C:32](=[O:49])[N:33]([C:39]2[CH:44]=[CH:43][CH:42]=[C:41]([C:45]([F:48])([F:46])[F:47])[CH:40]=2)[C:34]([CH3:38])=[C:35]([C:6]2[N:10]([C:11]3[CH:12]=[CH:13][C:14]([C:15]#[N:16])=[CH:17][CH:18]=3)[N:9]=[N:8][CH:7]=2)[CH:36]=1)=[O:30]

Participants

Conditions

Temperature: 100 °C

Procedure

4-(5-Tributylstannanyl-[1,2,3]triazol-1-yl)-benzonitrile (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 20 mg (40%) 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-ff7386d5b2894e74a11b699413b86dd3
Source dataset: uspto-grants-2011_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07998984B2

Reaction notes

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