Benzene, 1-chloro-4-ethynyl- → 5-[(4-chlorophenyl)ethynyl]-N,6-dimethyl-2-oxo-1-[3-(trifluoromethyl)phenyl]-1,2-dihydropyridine-3-carboxamide

HRID 1672607Notes

Reaction equation

HRID 1672607 reaction equation
I[C:2]1[CH:3]=[C:4]([C:20]([NH:22][CH3:23])=[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].[Cl:24][C:25]1[CH:30]=[CH:29][C:28]([C:31]#[CH:32])=[CH:27][CH:26]=1.CCN(C(C)C)C(C)C>C(#N)C.[Pd].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[Cu]I>[Cl:24][C:25]1[CH:30]=[CH:29][C:28]([C:31]#[C:32][C:2]2[CH:3]=[C:4]([C:20]([NH:22][CH3:23])=[O:21])[C:5](=[O:19])[N:6]([C:9]3[CH:14]=[CH:13][CH:12]=[C:11]([C:15]([F:18])([F:17])[F:16])[CH:10]=3)[C:7]=2[CH3:8])=[CH:27][CH:26]=1

Participants

7

Reactant 3

HCID 70118Benzene, 1-chloro-4-ethynyl-HCID 81531DiisopropylethylamineHCID 673427675-iodo-N,6-dimethyl-2-oxo-1-[3-(trifluoromethyl)phenyl]-1,2-dihydropyridine-3-carboxamide

Product 1

HCID 673461225-[(4-chlorophenyl)ethynyl]-N,6-dimethyl-2-oxo-1-[3-(trifluoromethyl)phenyl]-1,2-dihydropyridine-3-carboxamideYield 78%

Reagents, catalysts & solvents 3

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 11979704Tetrakis(triphenylphosphine)palladiumCatalystHCID 6342AcetonitrileSolvent

Conditions

Temperature
70 °C

Procedure

A mixture of 5-iodo-N,6-dimethyl-2-oxo-1-[3-(trifluoromethyl)phenyl]-1,2-dihydropyridine-3-carboxamide (139 mg, 0.32 mmol), tetrakis(triphenylphosphine) palladium(0) (1.8 mg, 1.6 μmol), copper(I) iodide (0.6 mg 3.2 μmol), 1-chloro-4-ethynylbenzene (87 mg, 0.638 mmol) and DIEA (64 mg, 0.5 mmol) in acetonitrile (1.5 ml) was heated in a microwave oven to 70° C. for 0.5 h. After cooling, the reaction mixture was purified by flash chromatography to give 5-[(4-chlorophenyl)ethynyl]-N,6-dimethyl-2-oxo-1-[3-(trifluoromethyl)phenyl]-1,2-dihydropyridine-3-carboxamide (111 mg, 78%).

Workup

  1. temperatureAfter cooling
  2. customthe reaction mixture was purified by flash chromatography

Sources & evidence

ORD record
ord-76a339c039be45a98393ccad9fab4aeb
Source dataset
uspto-grants-2011_08
Patent number
US07998984B2

Reaction notes

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