4-Benzyloxy-2(1H)-pyridone → tert-Butyl 2-(4-(benzyloxy)-2-oxopyridin-1(2H)-yl)-7,9-dimethyl-5,7,8,9-tetrahydro-6H-pyrido[3',4':4,5]pyrrolo[2,3-b]pyridine-6-carboxylate

HRID 882056Notes

Reaction equation

HRID 882056 reaction equation
Br[C:2]1[N:7]=[C:6]2[N:8]([CH3:23])[C:9]3[CH2:14][CH:13]([CH3:15])[N:12]([C:16]([O:18][C:19]([CH3:22])([CH3:21])[CH3:20])=[O:17])[CH2:11][C:10]=3[C:5]2=[CH:4][CH:3]=1.[CH2:24]([O:31][C:32]1[CH:37]=[CH:36][NH:35][C:34](=[O:38])[CH:33]=1)[C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1>>[CH2:24]([O:31][C:32]1[CH:37]=[CH:36][N:35]([C:2]2[N:7]=[C:6]3[N:8]([CH3:23])[C:9]4[CH2:14][CH:13]([CH3:15])[N:12]([C:16]([O:18][C:19]([CH3:22])([CH3:21])[CH3:20])=[O:17])[CH2:11][C:10]=4[C:5]3=[CH:4][CH:3]=2)[C:34](=[O:38])[CH:33]=1)[C:25]1[CH:26]=[CH:27][CH:28]=[CH:29][CH:30]=1

Participants

3

Reactant 2

HCID 36077244-Benzyloxy-2(1H)-pyridoneHCID 86667082tert-Butyl 2-bromo-7,9-dimethyl-5,7,8,9-tetrahydro-6H-pyrido[3',4':4,5]pyrrolo[2,3-b]pyridine-6-carboxylate

Product 1

HCID 67988843tert-Butyl 2-(4-(benzyloxy)-2-oxopyridin-1(2H)-yl)-7,9-dimethyl-5,7,8,9-tetrahydro-6H-pyrido[3',4':4,5]pyrrolo[2,3-b]pyridine-6-carboxylateYield 30%

Procedure

tert-Butyl 2-bromo-7,9-dimethyl-5,7,8,9-tetrahydro-6H-pyrido[3′,4′:4,5]pyrrolo[2,3-b]pyridine-6-carboxylate (enantiomer B) (100 mg, 0.263 mmol) and 4-(benzyloxy)pyridin-2(1H)-one (53 mg, 0.263 mmol) were reacted following the procedure for Example 2 (step e) to provide the title compound (39 mg, 30%) as a yellow oil: ESI MS m/z 501 [M+H]+.

Sources & evidence

ORD record
ord-aed4f1f8b1234d359d2083080a056373
Source dataset
uspto-grants-2015_03
Patent number
US08993765B2

Reaction notes

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