4-Benzyloxy-2(1H)-pyridone → tert-Butyl 7-(4-(benzyloxy)-2-oxopyridin-1(2H)-yl)-3,4-dihydropyrido[4',3':4,5]imidazo[1,2-a]pyridine-2(1H)-carboxylate

HRID 882067Notes

Reaction equation

HRID 882067 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.[CH2:22]([O:29][C:30]1[CH:35]=[CH:34][NH:33][C:32](=[O:36])[CH:31]=1)[C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1>>[CH2:22]([O:29][C:30]1[CH:35]=[CH:34][N:33]([C:2]2[CH:7]=[CH:6][N:5]3[C:8]4[CH2:14][N:13]([C:15]([O:17][C:18]([CH3:21])([CH3:20])[CH3:19])=[O:16])[CH2:12][CH2:11][C:9]=4[N:10]=[C:4]3[CH:3]=2)[C:32](=[O:36])[CH:31]=1)[C:23]1[CH:24]=[CH:25][CH:26]=[CH:27][CH:28]=1

Participants

3

Reactant 2

HCID 36077244-Benzyloxy-2(1H)-pyridoneHCID 67988849tert-Butyl 7-bromo-3,4-dihydropyrido[4',3':4,5]imidazo[1,2-a]pyridine-2(1H)-carboxylate

Product 1

HCID 67988851tert-Butyl 7-(4-(benzyloxy)-2-oxopyridin-1(2H)-yl)-3,4-dihydropyrido[4',3':4,5]imidazo[1,2-a]pyridine-2(1H)-carboxylateYield 61%

Procedure

tert-Butyl 7-bromo-3,4-dihydropyrido[4′,3′:4,5]imidazo[1,2-a]pyridine-2(1H)-carboxylate (591 mg, 1.68 mmol) and 4-(benzyloxy)pyridin-2(1H)-one (338 mg, 1.68 mmol) were reacted according to Example 18 (step g) to provide the title compound (482 mg, 61%) as a brown solid: ESI MS m/z 473 [M+H]+.

Sources & evidence

ORD record
ord-7e13e6aa0f3b46dd93605c05bd5cc6e2
Source dataset
uspto-grants-2015_03
Patent number
US08993765B2

Reaction notes

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