Benzoyl Peroxide → 2-[3-(5-bromooxazol-2-yl)benzyl]-6-(3,5-difluorophenyl)-2H-pyridazin-3-one

HRID 467509Notes

Reaction equation

HRID 467509 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([C:9]2[CH:10]=[CH:11][C:12](=[O:27])[N:13]([CH2:15][C:16]3[CH:21]=[CH:20][CH:19]=[C:18]([C:22]4[O:23][CH:24]=[CH:25][N:26]=4)[CH:17]=3)[N:14]=2)[CH:5]=[C:6]([F:8])[CH:7]=1.[Br:28]N1C(=O)CCC1=O.C(OOC(=O)C1C=CC=CC=1)(=O)C1C=CC=CC=1>ClC1C=CC=CC=1>[Br:28][C:24]1[O:23][C:22]([C:18]2[CH:17]=[C:16]([CH:21]=[CH:20][CH:19]=2)[CH2:15][N:13]2[C:12](=[O:27])[CH:11]=[CH:10][C:9]([C:4]3[CH:3]=[C:2]([F:1])[CH:7]=[C:6]([F:8])[CH:5]=3)=[N:14]2)=[N:26][CH:25]=1

Participants

5

Reactant 3

HCID 7187Benzoyl PeroxideHCID 67184N-bromobutanimideHCID 584972536-(3,5-difluorophenyl)-2-(3-oxazol-2-ylbenzyl)-2H-pyridazin-3-one

Product 1

HCID 584972522-[3-(5-bromooxazol-2-yl)benzyl]-6-(3,5-difluorophenyl)-2H-pyridazin-3-one

Reagents, catalysts & solvents 1

HCID 7964ChlorobenzeneSolvent

Procedure

A solution of 184 mg (0.504 mmol) of 6-(3,5-difluorophenyl)-2-(3-oxazol-2-ylbenzyl)-2H-pyridazin-3-one, 108 mg (0.605 mmol) of N-bromosuccinimide and 6.3 mg (0.026 mmol) of benzoyl peroxide in 1 ml of chlorobenzene is stirred at 80° C. for 42 hours. The reaction mixture is evaporated and chromatographed on a silica-gel column with dichloromethane/methanol as eluent, giving 2-[3-(5-bromooxazol-2-yl)benzyl]-6-(3,5-difluorophenyl)-2H-pyridazin-3-one as yellowish crystals; ESI 444, 446.

Workup

  1. customThe reaction mixture is evaporated
  2. customchromatographed on a silica-gel column with dichloromethane/methanol as eluent

Sources & evidence

ORD record
ord-b917a88f2a4d41009e8d1afbd8676d81
Source dataset
uspto-grants-2014_01
Patent number
US08623870B2

Reaction notes

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