4-Bromo-2-cyanopyridine → 2'-Cyano-6-methyl-[4,4']bipyridinyl-2-carboxylic acid (1-methyl-1H-pyrazol-3-yl)-amide

HRID 552519Notes

Reaction equation

HRID 552519 reaction equation
[CH3:1][N:2]1[CH:6]=[CH:5][C:4]([NH:7][C:8]([C:10]2[CH:15]=[C:14](B3OC(C)(C)C(C)(C)O3)[CH:13]=[C:12]([CH3:25])[N:11]=2)=[O:9])=[N:3]1.Br[C:27]1[CH:32]=[CH:31][N:30]=[C:29]([C:33]#[N:34])[CH:28]=1>>[CH3:1][N:2]1[CH:6]=[CH:5][C:4]([NH:7][C:8]([C:10]2[CH:15]=[C:14]([C:27]3[CH:32]=[CH:31][N:30]=[C:29]([C:33]#[N:34])[CH:28]=3)[CH:13]=[C:12]([CH3:25])[N:11]=2)=[O:9])=[N:3]1

Participants

3

Reactant 2

HCID 6932834-Bromo-2-cyanopyridineHCID 671639792-Methyl-6-((1-methyl-1H-pyrazol-3-yl)carbamoyl)pyridine-4-boronic acid pinacol ester

Product 1

HCID 248209762'-Cyano-6-methyl-[4,4']bipyridinyl-2-carboxylic acid (1-methyl-1H-pyrazol-3-yl)-amide

Procedure

The title compound, was prepared from 6-Methyl-4-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-pyridine-2-carboxylic acid (1-methyl-1H-pyrazol-3-yl)-amide in accordance with the general method of example 131, step 2 using 4-Bromo-2-cyanopyridine instead of 3-Trifluoromethyl-5-bromopyridine to yield the final compound as a white solid, MS (ISP): m/e=319.2 (M+H)+.

Sources & evidence

ORD record
ord-196a20afd90c4537b2053f3c359ca8fa
Source dataset
uspto-grants-2011_05
Patent number
US07951824B2

Reaction notes

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