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

HRID 882071Notes

Reaction equation

HRID 882071 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[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: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 497584672-Hydroxy-4-(4-trifluoromethylphenyl)pyridineHCID 67988849tert-Butyl 7-bromo-3,4-dihydropyrido[4',3':4,5]imidazo[1,2-a]pyridine-2(1H)-carboxylate

Product 1

HCID 68056804tert-Butyl 7-(2-oxo-4-(4-(trifluoromethyl)phenyl)pyridin-1(2H)-yl)-3,4-dihydropyrido[4',3':4,5]imidazo[1,2-a]pyridine-2 (1H)-carboxylateYield 64%

Procedure

tert-Butyl 7-bromo-3,4-dihydropyrido[4′,3′:4,5]imidazo[1,2-a]pyridine-2(1H)-carboxylate (150 mg, 0.426 mmol) and 4-(4-(trifluoromethyl)phenyl)pyridin-2(1H)-one (103 mg, 0.426 mmol) were reacted according to Example 18 (step g) to provide the title compound (138 mg, 64%) as a yellow solid: ESI MS m/z 511 [M+H]+.

Sources & evidence

ORD record
ord-c5feda04cfbd404ebacf6ae2158dd056
Source dataset
uspto-grants-2015_03
Patent number
US08993765B2

Reaction notes

Loading…