4-(6-(Trifluoromethyl)pyridin-3-yl)pyridin-2(1H)-one → tert-Butyl 7-(2-oxo-4-(6-(trifluoromethyl)pyridin-3-yl)pyridin-1(2H)-yl)-3,4-dihydropyrido[4',3':4,5]imidazo[1,2-a]pyridine-2 (1H)-carboxylate

HRID 882069Notes

Reaction equation

HRID 882069 reaction equation
Br[C:2]1[CH:7]=[CH:6][N:5]2[C:8]3[CH2:14][N:13]([C:15]([O:17][C:18]([CH3:21])([CH3:20])[CH3:19])=[O:16])[CH2:12][CH2:11][C:9]=3[N:10]=[C:4]2[CH:3]=1.[F:22][C:23]([F:38])([F:37])[C:24]1[N:29]=[CH:28][C:27]([C:30]2[CH:35]=[CH:34][NH:33][C:32](=[O:36])[CH:31]=2)=[CH:26][CH:25]=1>>[O:36]=[C:32]1[CH:31]=[C:30]([C:27]2[CH:28]=[N:29][C:24]([C:23]([F:38])([F:22])[F:37])=[CH:25][CH:26]=2)[CH:35]=[CH:34][N:33]1[C:2]1[CH:7]=[CH:6][N:5]2[C:8]3[CH2:14][N:13]([C:15]([O:17][C:18]([CH3:21])([CH3:20])[CH3:19])=[O:16])[CH2:12][CH2:11][C:9]=3[N:10]=[C:4]2[CH:3]=1

Participants

3

Reactant 2

HCID 579504694-(6-(Trifluoromethyl)pyridin-3-yl)pyridin-2(1H)-oneHCID 67988849tert-Butyl 7-bromo-3,4-dihydropyrido[4',3':4,5]imidazo[1,2-a]pyridine-2(1H)-carboxylate

Product 1

HCID 123146111tert-Butyl 7-(2-oxo-4-(6-(trifluoromethyl)pyridin-3-yl)pyridin-1(2H)-yl)-3,4-dihydropyrido[4',3':4,5]imidazo[1,2-a]pyridine-2 (1H)-carboxylateYield 55.2%

Procedure

tert-Butyl 7-bromo-3,4-dihydropyrido[4′,3′:4,5]imidazo[1,2-a]pyridine-2(1H)-carboxylate (212 mg, 0.602 mmol) and 4-(6-(trifluoromethyl)pyridin-3-yl)pyridin-2(1H)-one (145 mg, 0.604 mmol) were reacted according to Example 18 (step g) to provide the title compound (170 mg, 55%) as a white solid: ESI MS m/z 512 [M+H]+.

Sources & evidence

ORD record
ord-9bbb987ce0724327a2f84b3b7b84a6eb
Source dataset
uspto-grants-2015_03
Patent number
US08993765B2

Reaction notes

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