Benzonitrile, 3-(bromomethyl)- → HCID 70975706, compound

HRID 1190805Notes

Reaction equation

HRID 1190805 reaction equation
[CH3:1][N:2]1[C:6]2=[N:7][CH:8]=[CH:9][C:10]([N:11]3[CH2:16][CH2:15][CH2:14][C@@H:13]([NH:17][C:18](=[O:20])[OH:19])[CH2:12]3)=[C:5]2[NH:4][C:3]1=[O:21].Br[CH2:23][C:24]1[CH:25]=[C:26]([CH:29]=[CH:30][CH:31]=1)[C:27]#[N:28]>>[C:24]([O:20][C:18](=[O:19])[NH:17][C@@H:13]1[CH2:14][CH2:15][CH2:16][N:11]([C:10]2[CH:9]=[CH:8][N:7]=[C:6]3[N:2]([CH3:1])[C:3](=[O:21])[N:4]([CH2:23][C:24]4[CH:31]=[CH:30][CH:29]=[C:26]([C:27]#[N:28])[CH:25]=4)[C:5]=23)[CH2:12]1)([CH3:25])([CH3:31])[CH3:23]

Participants

3

Reactant 2

HCID 97249Benzonitrile, 3-(bromomethyl)-HCID 86673549HCID 86673549, compound

Product 1

HCID 70975706HCID 70975706, compoundYield 105.2%

Procedure

The specific operation referred to the step (5) described in Example 1 for details. 347 mg (R)-1-(3-methyl-2-oxo-2,3-dihydro-1H-imidazo[4,5-b]pyridin-7-yl)piperidin-3-yl carbamic acid ter.-butyl ester (1 mmol) and 235 mg 3-(bromomethyl)benzonitrile (1.2 mmol) were charged. A column chromatography was performed to afford 292 mg titled product with a yield of 63.2%.

Sources & evidence

ORD record
ord-d99ac6a5c8764da982b489b02de5230f
Source dataset
uspto-grants-2014_03
Patent number
US08680089B2

Reaction notes

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