2-Hydroxy-4-(4-trifluoromethylphenyl)pyridine → tert-Butyl 8-(2-oxo-4-(4-(trifluoromethyl)phenyl)pyridin-1(2H)-yl)-3,4-dihydropyrazino[1,2-a]benzimidazole-2(1H)-carboxylate

HRID 882064Notes

Reaction equation

HRID 882064 reaction equation
Br[C:2]1[CH:21]=[CH:20][C:5]2[N:6]3[CH2:12][CH2:11][N:10]([C:13]([O:15][C:16]([CH3:19])([CH3:18])[CH3:17])=[O:14])[CH2:9][C:7]3=[N:8][C:4]=2[CH:3]=1.[F:22][C:23]([F:38])([F:37])[C:24]1[CH: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]=[CH:29][C:24]([C:23]([F:37])([F:22])[F:38])=[CH:25][CH:26]=2)[CH:35]=[CH:34][N:33]1[C:2]1[CH:21]=[CH:20][C:5]2[N:6]3[CH2:12][CH2:11][N:10]([C:13]([O:15][C:16]([CH3:19])([CH3:18])[CH3:17])=[O:14])[CH2:9][C:7]3=[N:8][C:4]=2[CH:3]=1

Participants

3

Reactant 2

HCID 497584672-Hydroxy-4-(4-trifluoromethylphenyl)pyridineHCID 67988850tert-Butyl 8-bromo-3,4-dihydropyrazino[1,2-a]benzimidazole-2(1H)-carboxylate

Product 1

HCID 68056088tert-Butyl 8-(2-oxo-4-(4-(trifluoromethyl)phenyl)pyridin-1(2H)-yl)-3,4-dihydropyrazino[1,2-a]benzimidazole-2(1H)-carboxylateYield 7%

Procedure

tert-Butyl 8-bromo-3,4-dihydropyrazino[1,2-a]benzimidazole-2(1H)-carboxylate (150 mg, 0.426 mmol) and 4-(4-(trifluoromethyl)phenyl)pyridin-2(1H)-one (112 mg, 0.469 mmol) were reacted according to Example 18 (step g) to provide the title compound (15 mg, 7%) as a white solid: ESI MS m/z 511 [M+H]+.

Sources & evidence

ORD record
ord-2048d3ca780f4fff8299064f843f2f3c
Source dataset
uspto-grants-2015_03
Patent number
US08993765B2

Reaction notes

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