4-(Bromomethyl)benzonitrile → HCID 70841180, compound

HRID 1158954Notes

Reaction equation

HRID 1158954 reaction equation
[OH:1][C:2]1[C:3]([CH2:27][OH:28])=[C:4]([CH2:9][NH:10][C:11]([C:13]2[CH:18]=[CH:17][C:16]([C:19]3[CH:24]=[CH:23][C:22]([C:25]#[N:26])=[CH:21][CH:20]=3)=[CH:15][CH:14]=2)=[O:12])[CH:5]=[N:6][C:7]=1[CH3:8].Br[CH2:30][C:31]1[CH:36]=[CH:35][C:34]([C:37]#[N:38])=[CH:33][CH:32]=1>>[C:37]([C:34]1[CH:35]=[CH:36][C:31]([CH2:30][O:1][C:2]2[C:3]([CH2:27][OH:28])=[C:4]([CH2:9][NH:10][C:11]([C:13]3[CH:14]=[CH:15][C:16]([C:19]4[CH:20]=[CH:21][C:22]([C:25]#[N:26])=[CH:23][CH:24]=4)=[CH:17][CH:18]=3)=[O:12])[CH:5]=[N:6][C:7]=2[CH3:8])=[CH:32][CH:33]=1)#[N:38]

Participants

3

Reactant 2

HCID 869964-(Bromomethyl)benzonitrileHCID 59513910HCID 59513910, compound

Product 1

HCID 70841180HCID 70841180, compoundYield 75.5%

Procedure

The coupling of 4′-cyano-biphenyl-4-carboxylic acid (5-hydroxy-4-hydroxymethyl-6-methyl-pyridin-3-ylmethyl)-amide (64) (650 mg, 1.7 mmol) and α-bromo-p-tolunitrile (375 mg, 1.9 mmol), as described in Example 3, gave 4′-cyano-biphenyl-4-carboxylic acid (5-(4-cyano-benzyloxy)-4-hydroxymethyl-6-methyl-pyridin-3-ylmethyl)-amide (65) (627 mg, 74% yield).

Sources & evidence

ORD record
ord-86117c3fc6a240a1a3e738a9895c850c
Source dataset
uspto-grants-2010_10
Patent number
US07812037B2

Reaction notes

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