4-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)pyridine → HCID 57799383, compound

HRID 2101391Notes

Reaction equation

HRID 2101391 reaction equation
Br[C:2]1[C:3]([C:24]2[CH:29]=[CH:28][C:27]([Cl:30])=[CH:26][CH:25]=2)=[CH:4][C:5]2[N:6]([C:9](=[O:23])[N:10]([CH2:12][C:13]3[CH:14]=[N:15][C:16]([C:19]([F:22])([F:21])[F:20])=[CH:17][CH:18]=3)[N:11]=2)[C:7]=1[CH3:8].CC1(C)C(C)(C)OB([C:39]2[CH:44]=[CH:43][N:42]=[CH:41][CH:40]=2)O1.CC1C(CN2C(=O)N3C=CC(C4C=CC(C#N)=CC=4)=C(C4C=CC=CC=4)C3=N2)=CC=C(C(F)(F)F)N=1>>[Cl:30][C:27]1[CH:26]=[CH:25][C:24]([C:3]2[C:2]([C:39]3[CH:44]=[CH:43][N:42]=[CH:41][CH:40]=3)=[C:7]([CH3:8])[N:6]3[C:9](=[O:23])[N:10]([CH2:12][C:13]4[CH:14]=[N:15][C:16]([C:19]([F:22])([F:20])[F:21])=[CH:17][CH:18]=4)[N:11]=[C:5]3[CH:4]=2)=[CH:29][CH:28]=1

Participants

4

Reactant 3

HCID 27346484-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)pyridineHCID 16004909HCID 16004909, compoundHCID 577994276-bromo-7-(4-chlorophenyl)-5-methyl-2-((6-(trifluoromethyl)pyridin-3-yl)methyl)-[1,2,4]triazolo[4,3-a]pyridin-3(2H)-one

Product 1

HCID 57799383HCID 57799383, compoundYield 64.5%

Procedure

The title compound (16 mg, 64%) as a light yellow powder was prepared from 6-bromo-7-(4-chlorophenyl)-5-methyl-2-((6-(trifluoromethyl)pyridin-3-yl)methyl)-[1,2,4]triazolo[4,3-a]pyridin-3(2H)-one (25 mg, 0.05 mmol) and 4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridine (42.5 mg, 0.2 mmol) by procedures analogous to those used for the preparation of 4-(2-((2-methyl-6-(trifluoromethyl)pyridin-3-yl)methyl)-3-oxo-8-phenyl-2,3-dihydro-[1,2,4]triazolo[4,3-a]pyridin-7-yl)benzonitrile. HPLC/MS: retention time=2.87 min, [M+H]+=496.4.

Sources & evidence

ORD record
ord-d67e2caa9ae74abb96b6f00cfafe200d
Source dataset
uspto-grants-2009_08
Patent number
US07572808B2

Reaction notes

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