Benzonitrile, 3-(bromomethyl)- → HCID 58636708, compound

HRID 1158976Notes

Reaction equation

HRID 1158976 reaction equation
[CH3:1][O:2][C:3](=[O:31])[CH2:4][CH2:5][C:6]1[C:11]([CH2:12][N:13]([C:22]([O:24][C:25]([CH3:28])([CH3:27])[CH3:26])=[O:23])[C:14]2[CH:19]=[CH:18][C:17]([C:20]#[N:21])=[CH:16][CH:15]=2)=[CH:10][N:9]=[C:8]([CH3:29])[C:7]=1[OH:30].Br[CH2:33][C:34]1[CH:39]=[CH:38][CH:37]=[C:36]([C:40]#[N:41])[CH:35]=1>>[CH3:1][O:2][C:3](=[O:31])[CH2:4][CH2:5][C:6]1[C:11]([CH2:12][N:13]([C:22]([O:24][C:25]([CH3:26])([CH3:27])[CH3:28])=[O:23])[C:14]2[CH:19]=[CH:18][C:17]([C:20]#[N:21])=[CH:16][CH:15]=2)=[CH:10][N:9]=[C:8]([CH3:29])[C:7]=1[O:30][CH2:33][C:34]1[CH:39]=[CH:38][CH:37]=[C:36]([C:40]#[N:41])[CH:35]=1

Participants

3

Reactant 2

HCID 97249Benzonitrile, 3-(bromomethyl)-HCID 58636832HCID 58636832, compound

Product 1

HCID 58636708HCID 58636708, compoundYield 68%

Procedure

The coupling of 3-(5-{[tert-butoxycarbonyl-(4-cyano-phenyl)-amino]-methyl}-3-hydroxy-2-methyl-pyridin-4-yl)-propionic acid methyl ester (121) and α-bromo-m-tolunitrile (102 mg, 0.5 mmol), as described in Example 1, gave 3-[5-{[tert-butoxycarbonyl-(4-cyano-phenyl)-amino]-methyl}-3-(3-cyano-benzyloxy)-2-methyl-pyridin-4-yl]-propionic acid methyl ester (122) (162 mg, 68% yield for 2 steps).

Sources & evidence

ORD record
ord-b225736655b8461aab5231f6c9dfb9da
Source dataset
uspto-grants-2010_10
Patent number
US07812037B2

Reaction notes

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