4-(Bromomethyl)benzonitrile → HCID 68644168, compound

HRID 1158977Notes

Reaction equation

HRID 1158977 reaction equation
[C:1]([O:5][C:6](=[O:27])[N:7]([C:19]1[CH:24]=[CH:23][C:22]([C:25]#[N:26])=[CH:21][CH:20]=1)[CH2:8][C:9]1[CH:10]=[N:11][C:12]([CH3:18])=[C:13]([OH:17])[C:14]=1[CH2:15][OH:16])([CH3:4])([CH3:3])[CH3:2].Br[CH2:29][C:30]1[CH:35]=[CH:34][C:33]([C:36]#[N:37])=[CH:32][CH:31]=1>>[C:1]([O:5][C:6](=[O:27])[N:7]([CH2:8][C:9]1[CH:10]=[N:11][C:12]([CH3:18])=[C:13]([O:17][CH2:29][C:30]2[CH:35]=[CH:34][C:33]([C:36]#[N:37])=[CH:32][CH:31]=2)[C:14]=1[CH2:15][OH:16])[C:19]1[CH:20]=[CH:21][C:22]([C:25]#[N:26])=[CH:23][CH:24]=1)([CH3:4])([CH3:2])[CH3:3]

Participants

3

Reactant 2

HCID 869964-(Bromomethyl)benzonitrileHCID 58636800HCID 58636800, compound

Product 1

HCID 68644168HCID 68644168, compoundYield 70.3%

Procedure

The coupling of (4-cyano-phenyl)-(5-hydroxy-4-hydroxymethyl-6-methyl-pyridin-3-ylmethyl)-carbamic acid tert-butyl ester (105) (137.0 g, 0.37 mole) and α-bromo-p-tolunitrile (72.7 g, 370 mmol), as described in Example 1, gave [5-(4-cyano-benzyloxy)-4-hydroxymethyl-6-methyl-pyridin-3-ylmethyl]-(4-cyano-phenyl)-carbamic acid tert-butyl ester (124) (126.0 g, 70% yield) as a colorless solid.

Sources & evidence

ORD record
ord-089b6e068a3f42fc82b70cd9f326ea01
Source dataset
uspto-grants-2010_10
Patent number
US07812037B2

Reaction notes

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