N-(3-(1H-imidazol-1-yl)-5-(trifluoromethyl)phenyl)-3-iodo-4-methylbenzamide → N-(3-(1H-imidazol-1-yl)-5-(trifluoromethyl)phenyl)-3-(imidazo[1,2-a]pyridin-3-ylethynyl)-4-methylbenzamide

HRID 1640477Notes

Reaction equation

HRID 1640477 reaction equation
[N:1]1([C:6]2[CH:7]=[C:8]([NH:16][C:17](=[O:26])[C:18]3[CH:23]=[CH:22][C:21]([CH3:24])=[C:20](I)[CH:19]=3)[CH:9]=[C:10]([C:12]([F:15])([F:14])[F:13])[CH:11]=2)[CH:5]=[CH:4][N:3]=[CH:2]1.[C:27]([C:29]1[N:33]2[CH:34]=[CH:35][CH:36]=[CH:37][C:32]2=[N:31][CH:30]=1)#[CH:28]>>[N:1]1([C:6]2[CH:7]=[C:8]([NH:16][C:17](=[O:26])[C:18]3[CH:23]=[CH:22][C:21]([CH3:24])=[C:20]([C:28]#[C:27][C:29]4[N:33]5[CH:34]=[CH:35][CH:36]=[CH:37][C:32]5=[N:31][CH:30]=4)[CH:19]=3)[CH:9]=[C:10]([C:12]([F:15])([F:14])[F:13])[CH:11]=2)[CH:5]=[CH:4][N:3]=[CH:2]1

Participants

3

Reactant 2

HCID 44222638N-(3-(1H-imidazol-1-yl)-5-(trifluoromethyl)phenyl)-3-iodo-4-methylbenzamideHCID 468387593-Ethynylimidazo[1,2-a]pyridine

Product 1

HCID 24826632N-(3-(1H-imidazol-1-yl)-5-(trifluoromethyl)phenyl)-3-(imidazo[1,2-a]pyridin-3-ylethynyl)-4-methylbenzamide

Procedure

The titled compound was made as for example 1 using N-(3-(1H-imidazol-1-yl)-5-(trifluoromethyl)phenyl)-3-iodo-4-methylbenzamide and 3-ethynylimidazo[1,2-a]pyridine: MS (M+H)+ 486. The titled compound can also be prepared according to the alternative synthesis described in example 1 from 3-(imidazo[1,2-a]pyridin-3-ylethynyl)-4-methylbenzoic acid and 3-(1H-imidazol-1-yl)-5-(trifluoromethyl)aniline (as prepared in Example 1). The 3-(imidazo[1,2-a]pyridin-3-ylethynyl)-4-methylbenzoic acid is prepared in a manner similar to that described in Example 1 using 3-Ethynylimidazo[1,2-a]pyridine and 3-iodo-4-methylbenzoic acid as Sonogashira coupling partners.

Sources & evidence

ORD record
ord-f4917bdbd45a4da6ab2f8adcf440f1e1
Source dataset
uspto-grants-2012_02
Patent number
US08114874B2

Reaction notes

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