4-(Bromomethyl)benzonitrile → 3-[3-(4-Cyano-benzyloxy)-5-hydroxymethyl-2-methyl-pyridin-4-yl]-propionic acid ethyl ester

HRID 1158945Notes

Reaction equation

HRID 1158945 reaction equation
[CH2:1]([O:3][C:4](=[O:17])[CH2:5][CH2:6][C:7]1[C:12]([CH2:13][OH:14])=[CH:11][N:10]=[C:9]([CH3:15])[C:8]=1[OH:16])[CH3:2].Br[CH2:19][C:20]1[CH:25]=[CH:24][C:23]([C:26]#[N:27])=[CH:22][CH:21]=1>>[CH2:1]([O:3][C:4](=[O:17])[CH2:5][CH2:6][C:7]1[C:12]([CH2:13][OH:14])=[CH:11][N:10]=[C:9]([CH3:15])[C:8]=1[O:16][CH2:19][C:20]1[CH:25]=[CH:24][C:23]([C:26]#[N:27])=[CH:22][CH:21]=1)[CH3:2]

Participants

3

Reactant 2

HCID 869964-(Bromomethyl)benzonitrileHCID 586367193-(3-Hydroxy-5-hydroxymethyl-2-methyl-pyridin-4-yl)-propionic acid ethyl ester

Product 1

HCID 686441863-[3-(4-Cyano-benzyloxy)-5-hydroxymethyl-2-methyl-pyridin-4-yl]-propionic acid ethyl esterYield 70%

Procedure

The coupling of 3-(3-hydroxy-5-hydroxymethyl-2-methyl-pyridin-4-yl)-propionic acid ethyl ester (35) (3.4 g, 14.2 mmol) and α-bromo-p-tolunitrile (4.2 g, 21.4 mmol), as described in Example 1, gave 3-[3-(4-cyano-benzyloxy)-5-hydroxymethyl-2-methyl-pyridin-4-yl]-propionic acid ethyl ester (36) (3.5 g, 70% yield).

Sources & evidence

ORD record
ord-1118b35afd184f309ac75714d484dd12
Source dataset
uspto-grants-2010_10
Patent number
US07812037B2

Reaction notes

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