Pyridine N-Oxide → 5-Bromo-2-(3-chloro-4-fluorobenzyl)-8-methoxy-2,3,4,6-tetrahydro-2,6-naphthyridine-1,7-dione

HRID 1817364Notes

Reaction equation

HRID 1817364 reaction equation
[Br:1][C:2]1[N:11]=[CH:10][C:9]([O:12][CH3:13])=[C:8]2[C:3]=1[CH2:4][CH2:5][N:6]([CH2:15][C:16]1[CH:21]=[CH:20][C:19]([F:22])=[C:18]([Cl:23])[CH:17]=1)[C:7]2=[O:14].[N+]1([O-:30])C=CC=CC=1>>[Br:1][C:2]1[NH:11][C:10](=[O:30])[C:9]([O:12][CH3:13])=[C:8]2[C:3]=1[CH2:4][CH2:5][N:6]([CH2:15][C:16]1[CH:21]=[CH:20][C:19]([F:22])=[C:18]([Cl:23])[CH:17]=1)[C:7]2=[O:14]

Participants

3

Reactant 2

HCID 12753Pyridine N-OxideHCID 86613908HCID 86613908, compound

Product 1

HCID 690618815-Bromo-2-(3-chloro-4-fluorobenzyl)-8-methoxy-2,3,4,6-tetrahydro-2,6-naphthyridine-1,7-dione

Procedure

5-Bromo-2-(3-chloro-4-fluorobenzyl)-8-methoxy-2,3,4,6-tetrahydro-2,6-naphthyridine-1,7-dione was prepared in a manner similar to that described in Example 12, step 7 to 9, except the oxidation of 5-bromo-2-(3-chloro-4-fluorobenzyl)-8-methoxy-3,4-dihydro-2,6-naphthyridin-1(2H)-one to the corresponding pyridine N-oxide was oxidized with hydrogen peroxide urea complex (Caron et al., Tetrahedron Lett., 2299, 2000).

Sources & evidence

ORD record
ord-6a06e3002e1f4d92b34baf2ad3dfb3b1
Source dataset
uspto-grants-2009_10
Patent number
US07598264B2

Reaction notes

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