N-bromobutanimide → HCID 86714169, compound

HRID 920011Notes

Reaction equation

HRID 920011 reaction equation
[CH3:1][O:2][C:3]([C:5]1[C:6]([OH:31])=[C:7]2[C:12](=[CH:13][N:14]=1)[N:11]([CH2:15][C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1)[C:10](=[O:22])[C:9]([C:23]1[CH:28]=[CH:27][C:26]([O:29][CH3:30])=[CH:25][CH:24]=1)=[CH:8]2)=[O:4].[Br:32]N1C(=O)CCC1=O>C(Cl)Cl>[CH3:1][O:2][C:3]([C:5]1[C:6]([OH:31])=[C:7]2[C:12](=[C:13]([Br:32])[N:14]=1)[N:11]([CH2:15][C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1)[C:10](=[O:22])[C:9]([C:23]1[CH:24]=[CH:25][C:26]([O:29][CH3:30])=[CH:27][CH:28]=1)=[CH:8]2)=[O:4]

Participants

4

Reactant 2

HCID 67184N-bromobutanimideHCID 68297680HCID 68297680, compound

Product 1

HCID 86714169HCID 86714169, compoundYield 69.7%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A mixture of 1-benzyl-5-hydroxy-3-(4-methoxy-phenyl)-2-oxo-1,2-dihydro-[1,7]naphthyridine-6-carboxylic acid methyl ester (93 mg, 0.22 mmol) and N-bromosuccinimide (44 mg, 0.25 mmol) in CH2Cl2 (0.8 mL) was refluxed for 3 h. Solvent was evaporated in vacuo, and the residue was purified by silica gel chromatography (5-30% EtOAc/hexanes+1% AcOH) to give 76 mg of the title compound as a yellow solid. MS: (+) m/z 495.21, 497.10 (M+1, 79/81Br).

Workup

  1. temperaturewas refluxed for 3 h
  2. customSolvent was evaporated in vacuo
  3. customthe residue was purified by silica gel chromatography (5-30% EtOAc/hexanes+1% AcOH)

Sources & evidence

ORD record
ord-bda34a7d184144b2b267891aa070d024
Source dataset
uspto-grants-2016_03
Patent number
US09271970B2

Reaction notes

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