1-Ethynyl-4-(trifluoromethyl)benzene → 3-(1,1-Difluoro-2-methoxyethyl)-6-((4-(trifluoromethyl)phenyl)ethynyl)-[1,2,4]triazolo[4,3-a]pyridine

HRID 406444

Reaction equation

Br[C:2]1[CH:3]=[CH:4][C:5]2[N:6]([C:8]([C:11]([F:16])([F:15])[CH2:12][O:13][CH3:14])=[N:9][N:10]=2)[CH:7]=1.[C:17]([C:19]1[CH:24]=[CH:23][C:22]([C:25]([F:28])([F:27])[F:26])=[CH:21][CH:20]=1)#[CH:18]>C1COCC1.[Cu]I>[F:15][C:11]([C:8]1[N:6]2[CH:7]=[C:2]([C:18]#[C:17][C:19]3[CH:24]=[CH:23][C:22]([C:25]([F:26])([F:27])[F:28])=[CH:21][CH:20]=3)[CH:3]=[CH:4][C:5]2=[N:10][N:9]=1)([F:16])[CH2:12][O:13][CH3:14]

Participants

Conditions

Temperature: 70 °C

Procedure

To a stirred solution of 6-bromo-3-(1,1-difluoro-2-methoxyethyl)-[1,2,4]triazolo[4,3-a]pyridine (46 mg, 0.16 mmol) in THF (5 mL) was added catalytic amount of dichlorobis(triphenylphosphine) palladium(II) (11 mg) and copper(I) iodide (3 mg), followed by 1-ethynyl-4-(trifluoromethyl)benzene (41 mg, 0.24 mmol). The resulting mixture was flushed with N2 and Et3N (2 mL) was added. The reaction mixture was stirred at 70° C. overnight and purified by prep-TLC (EtOAc: hexanes=2:3) followed by HPLC to give 3-(1,1-difluoro-2-methoxyethyl)-6-((4-(trifluoromethyl)phenyl)ethynyl)-[1,2,4]triazolo[4,3-a]pyridine.

Workup

customThe resulting mixture was flushed with N2 and Et3N (2 mL)
additionwas added
custompurified by prep-TLC (EtOAc: hexanes=2:3)

Sources & evidence

ORD record: ord-b90f0c8d8a514419babce827e758a1e5
Source dataset: uspto-grants-2014_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08754103B2

Linked notes

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