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

HRID 882070Notes

Reaction equation

HRID 882070 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:40])([F:39])[C:24]1[N:29]=[CH:28][C:27]([CH2:30][O:31][C:32]2[CH:37]=[CH:36][NH:35][C:34](=[O:38])[CH:33]=2)=[CH:26][CH:25]=1>>[O:38]=[C:34]1[CH:33]=[C:32]([O:31][CH2:30][C:27]2[CH:28]=[N:29][C:24]([C:23]([F:40])([F:22])[F:39])=[CH:25][CH:26]=2)[CH:37]=[CH:36][N:35]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 579503604-((6-(Trifluoromethyl)pyridin-3-yl)methoxy)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 68056129tert-Butyl 7-(2-oxo-4-((6-(trifluoromethyl)pyridin-3-yl)methoxy)pyridin-1(2H)-yl)-3,4-dihydropyrido[4',3':4,5]imidazo[1,2-a]pyridine-2(1H)-carboxylateYield 44%

Procedure

tert-Butyl 7-bromo-3,4-dihydropyrido[4′,3′:4,5]imidazo[1,2-a]pyridine-2(1H)-carboxylate (175 mg, 0.498 mmol) and 4-((6-(trifluoromethyl)pyridin-3-yl)methoxy)pyridin-2(1H)-one (134 mg, 0.498 mmol) were reacted according to Example 18 (step g) to provide the title compound (104 mg, 44%) as a yellow solid: ESI MS m/z 542 [M+H]+.

Sources & evidence

ORD record
ord-f4158e8e8446427da830ad08f795738a
Source dataset
uspto-grants-2015_03
Patent number
US08993765B2

Reaction notes

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