4-Bromo-2-cyanobenzoic acid → 5-Bromo-2-[4-(3,5,6-trimethylpyridin-2-yl)piperazine-1-carbonyl]benzonitrile

HRID 2411308Notes

Reaction equation

HRID 2411308 reaction equation
[Br:1][C:2]1[CH:10]=[CH:9][C:5]([C:6]([OH:8])=O)=[C:4]([C:11]#[N:12])[CH:3]=1.[CH3:13][C:14]1[C:15]([N:22]2[CH2:27][CH2:26][NH:25][CH2:24][CH2:23]2)=[N:16][C:17]([CH3:21])=[C:18]([CH3:20])[CH:19]=1>>[Br:1][C:2]1[CH:10]=[CH:9][C:5]([C:6]([N:25]2[CH2:26][CH2:27][N:22]([C:15]3[C:14]([CH3:13])=[CH:19][C:18]([CH3:20])=[C:17]([CH3:21])[N:16]=3)[CH2:23][CH2:24]2)=[O:8])=[C:4]([CH:3]=1)[C:11]#[N:12]

Participants

3

Reactant 2

HCID 584845854-Bromo-2-cyanobenzoic acidHCID 584848231-(3,5,6-Trimethylpyridin-2-yl)piperazine

Product 1

HCID 712521745-Bromo-2-[4-(3,5,6-trimethylpyridin-2-yl)piperazine-1-carbonyl]benzonitrileYield 87.9%

Procedure

Using 4-bromo-2-cyanobenzoic acid (3.84 g) described in Preparation Example 76 and 1-(3,5,6-trimethylpyridin-2-yl)piperazine (3.66 g) described in Preparation Example 92 and by the reaction and treatment in the same manner as in Preparation Example 111, the title compound (6.17 g) was obtained.

Workup

  1. customdescribed in Preparation Example 92 and by the reaction and treatment in the same manner as in Preparation Example 111

Sources & evidence

ORD record
ord-40e72af43e344d2ebe3ba2aeb4fbf94e
Source dataset
uspto-grants-2014_08
Patent number
US08816079B2

Reaction notes

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