Azobisisobutyronitrile → HCID 68799492, compound

HRID 1370287Notes

Reaction equation

HRID 1370287 reaction equation
[CH2:1]([O:3][C:4]([C:6]1[C:15](=[O:16])[C:14]2[C:9](=[CH:10][C:11]([Br:18])=[C:12]([CH3:17])[CH:13]=2)[N:8]([CH2:19][C:20]2[C:25]([F:26])=[CH:24][CH:23]=[CH:22][C:21]=2[F:27])[CH:7]=1)=[O:5])[CH3:2].C1C(=O)N([Br:35])C(=O)C1.N(C(C)(C)C#N)=NC(C)(C)C#N.C(OCC)(=O)C>C(Cl)Cl>[CH2:1]([O:3][C:4]([C:6]1[C:15](=[O:16])[C:14]2[C:9](=[CH:10][C:11]([Br:18])=[C:12]([CH2:17][Br:35])[CH:13]=2)[N:8]([CH2:19][C:20]2[C:25]([F:26])=[CH:24][CH:23]=[CH:22][C:21]=2[F:27])[CH:7]=1)=[O:5])[CH3:2]

Participants

6

Reactant 4

HCID 6547AzobisisobutyronitrileHCID 8857Ethyl AcetateHCID 67184N-bromobutanimide2×HCID 15462231HCID 15462231, compound

Product 1

HCID 68799492HCID 68799492, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A mixture of 7-bromo-1-(2,6-difluorobenzyl)-1,4-dihydro-6-methyl-4-oxoquinoline-3-carboxylic acid ethyl ester (3.5 g, 8 mmol), prepared according to the procedure outlined in PCT application WO97/14682, Reference Example 3, NBS (1.5 g, 8.4 mmol) and 2,2′-azobisisobutyronitrile (AIBN, 100 mg) in DCM (200 mL) was stirred at reflux for 4 h. Additional NBS (750 mg) was added and the mixture was refluxed for 4 h. Column chromatography (hexanes:ethyl acetate=3:7) yielded the product as a white solid.

Workup

  1. customprepared
  2. temperatureat reflux for 4 h
  3. temperaturethe mixture was refluxed for 4 h

Sources & evidence

ORD record
ord-8d6f5b1cb282432eaec41b40179dee0c
Source dataset
uspto-grants-2003_06
Patent number
US06583153B2

Reaction notes

Loading…