2-Bromo-3-methylpyridine → HCID 22493253, compound

HRID 1816281Notes

Reaction equation

HRID 1816281 reaction equation
Br[C:2]1[C:7]([CH3:8])=[CH:6][CH:5]=[CH:4][N:3]=1.B(O)(O)[C:10]1[C:15]([NH:16][C:17]([O:19][C:20]([CH3:23])([CH3:22])[CH3:21])=[O:18])=[CH:14][CH:13]=[CH:12][CH:11]=1>>[CH3:8][C:7]1[C:2]([C:14]2[CH:13]=[CH:12][CH:11]=[CH:10][C:15]=2[NH:16][C:17](=[O:18])[O:19][C:20]([CH3:22])([CH3:21])[CH3:23])=[N:3][CH:4]=[CH:5][CH:6]=1

Participants

3

Reactant 2

HCID 2208322-Bromo-3-methylpyridineHCID 2773226(2-BOC-aminophenyl)boronic acid

Product 1

HCID 22493253HCID 22493253, compoundYield 132.3%

Procedure

2-Bromo-3-methylpyridine (0.65 g, 3.8 mmol) and N-(tert-butoxycarbonyl)-2-amino-1-phenylboronic acid (0.90 g, 3.8 mmol), prepared according to the method described by J. J. S. Lambda and J. M. Tour in J. Am. Chem. SDC., 1994,116,11723-11736, were coupled as in Example 70 (also see J. Org. Chem., 1995, 60, 292), to give 1.43 g of crude tert-butyl 2-(3-methyl-2-pyridinyl)phenylcarbamate, which was deprotected as in Example 75 to give 0.45 g of 2-(3-methyl-2-pyridinyl)aniline.

Sources & evidence

ORD record
ord-21c292af79754dc4b4d2cbc13b197884
Source dataset
uspto-grants-2005_04
Patent number
US06884801B1

Reaction notes

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