Potassium Carbonate → 3-((7-(4-chlorophenyl)-3-oxo-8-(pyridin-4-yl)-[1,2,4]triazolo[4,3-a]pyridin-2(3H)-yl)methyl)-2-methyl-6-(trifluoromethyl)pyridine 1-oxide

HRID 2101336

Reaction equation

HRID 2101336 reaction equation
Br[C:2]1[C:3]2[N:4]([C:15](=[O:18])[NH:16][N:17]=2)[CH:5]=[CH:6][C:7]=1[C:8]1[CH:13]=[CH:12][C:11]([Cl:14])=[CH:10][CH:9]=1.Br[CH2:20][C:21]1[C:22]([CH3:32])=[N+:23]([O-:31])[C:24]([C:27]([F:30])([F:29])[F:28])=[CH:25][CH:26]=1.C(=O)([O-])[O-].[K+].[K+]>CN(C)C=O>[Cl:14][C:11]1[CH:12]=[CH:13][C:8]([C:7]2[CH:6]=[CH:5][N:4]3[C:15](=[O:18])[N:16]([CH2:20][C:21]4[C:22]([CH3:32])=[N+:23]([O-:31])[C:24]([C:27]([F:30])([F:29])[F:28])=[CH:25][CH:26]=4)[N:17]=[C:3]3[C:2]=2[C:7]2[CH:6]=[CH:5][N:4]=[CH:3][CH:2]=2)=[CH:9][CH:10]=1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 577994388-Bromo-7-(4-chlorophenyl)[1,2,4]triazolo[4,3-a]pyridin-3(2H)-oneHCID 598348003-(Bromomethyl)-2-methyl-6-(trifluoromethyl)pyridine 1-oxide

Product 1

HCID 577993553-((7-(4-chlorophenyl)-3-oxo-8-(pyridin-4-yl)-[1,2,4]triazolo[4,3-a]pyridin-2(3H)-yl)methyl)-2-methyl-6-(trifluoromethyl)pyridine 1-oxide

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

The title compound was also prepared from 8-bromo-7-(4-chlorophenyl)-[1,2,4]triazolo[4,3-a]pyridin-3(2H)-one by treatment with 3-(bromomethyl)-2-methyl-6-(trifluoromethyl)pyridine 1-oxide and potassium carbonate in N,N-dimethylformamide at 70° C., followed by treatment with 4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridine and aqueous potassium carbonate solution in toluene under (Ph3P)4Pd catalysis at 100° C.

Sources & evidence

ORD record
ord-9690ee447ccc4913b5ffd6bea60dde72
Source dataset
uspto-grants-2009_08
Patent number
US07572808B2

Linked notes

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