6-Bromopyridine-2-carboxylic acid → 6-(2-Aminophenyl)pyridine-2-carboxylic acid

HRID 1526160Notes

Reaction equation

HRID 1526160 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1B(O)O.Br[C:12]1[N:17]=[C:16]([C:18]([OH:20])=[O:19])[CH:15]=[CH:14][CH:13]=1>>[NH2:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:12]1[N:17]=[C:16]([C:18]([OH:20])=[O:19])[CH:15]=[CH:14][CH:13]=1

Participants

3

Reactant 2

HCID 5939196-Bromopyridine-2-carboxylic acidHCID 2773216(2-Aminophenyl)boronic acid

Product 1

HCID 341784146-(2-Aminophenyl)pyridine-2-carboxylic acid

Procedure

Preparation analogous to Ex. 10, A, using 110 mmol of 2-aminophenylboronic acid [5570-18-3] instead of 110 mmol of 3-carboxybenzeneboronic acid, and using 100 mmol of 6-bromopyridine-2-carboxylic acid [21190-87-4] instead of 100 mmol of 1-bromo-2-aminonaphthalene. Yield: 17.5 g (82 mmol), 81.7%; purity according to 1H-NMR about 99%.

Workup

  1. customPreparation analogous to Ex

Sources & evidence

ORD record
ord-3543a43eb29b4679b41893375547e677
Source dataset
uspto-grants-2015_07
Patent number
US09085579B2

Reaction notes

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