Benzonitrile, 3-(bromomethyl)- → HCID 58636738, compound

HRID 1158969Notes

Reaction equation

HRID 1158969 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][CH:33]=[C:32]([C:36]#[N:37])[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][CH:33]=[C:32]([C:36]#[N:37])[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 97249Benzonitrile, 3-(bromomethyl)-HCID 58636800HCID 58636800, compound

Product 1

HCID 58636738HCID 58636738, compoundYield 122.4%

Procedure

The coupling of (4-cyano-phenyl)-(5-hydroxy-4-hydroxymethyl-6-methyl-pyridin-3-ylmethyl)-carbamic acid tert-butyl ester (105) (8.7 g, 19.9 mmol) and α-bromo-m-tolunitrile (5.6 g, 28 mmol), as described in Example 1, gave [5-(3-cyano-benzyloxy)-4-hydroxymethyl-6-methyl-pyridin-3-ylmethyl]-(4-cyano-phenyl)-carbamic acid tert-butyl ester (106) (11.8 g, 68% yield).

Sources & evidence

ORD record
ord-ac9e56c7ebbf49a2966aadc6832871ef
Source dataset
uspto-grants-2010_10
Patent number
US07812037B2

Reaction notes

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