N-bromobutanimide → 4-Bromo-2-(4-fluoro-phenyl)-5-[2-(4-fluoro-phenyl)-ethyl]-1-methyl-1,2-dihydro-pyrazol-3-one

HRID 1993925ノート

反応式

HRID 1993925 の反応式
[F:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]2[C:12](=[O:13])[CH:11]=[C:10]([CH2:14][CH2:15][C:16]3[CH:21]=[CH:20][C:19]([F:22])=[CH:18][CH:17]=3)[N:9]2[CH3:23])=[CH:4][CH:3]=1.[Br:24]N1C(=O)CCC1=O>C(Cl)Cl.[Al]>[Br:24][C:11]1[C:12](=[O:13])[N:8]([C:5]2[CH:4]=[CH:3][C:2]([F:1])=[CH:7][CH:6]=2)[N:9]([CH3:23])[C:10]=1[CH2:14][CH2:15][C:16]1[CH:17]=[CH:18][C:19]([F:22])=[CH:20][CH:21]=1

参加物

5

反応物 2

HCID 67184N-bromobutanimideHCID 686794792-(4-Fluoro-phenyl)-5-[2-(4-fluoro-phenyl)-ethyl]-1-methyl-1,2-dihydro-pyrazol-3-one

生成物 1

HCID 686775324-Bromo-2-(4-fluoro-phenyl)-5-[2-(4-fluoro-phenyl)-ethyl]-1-methyl-1,2-dihydro-pyrazol-3-one収率 84.3%

試薬・触媒・溶媒 2

HCID 6344Dichloromethane溶媒HCID 5359268Aluminum溶媒

実験手順

To a solution of 2-(4-fluoro-phenyl)-5-[2-(4-fluoro-phenyl)-ethyl]-1-methyl-1,2-dihydro-pyrazol-3-one (0.296 g) in methylene chloride (5 mL) was added N-bromosuccinimide (0.168 g). The reaction vessel was wrapped in aluminium foil and stirred for 24 hours. The solvent was evaporated in vacuo and the residue was dissolved in EtOAc and water. The phases were separated and the aqueous phase was extracted with more EtOAc. The combined organic phases were washed with brine, dried over sodium sulfate, filtered and reduced in vacuo to give a crude residue. Flash column chromatography over silica gel using ISCO combiflash chromatography and eluting with EtOAc/heptane afforded the desired 4-bromo-2-(4-fluoro-phenyl)-5-[2-(4-fluoro-phenyl)-ethyl]-1-methyl-1,2-dihydro-pyrazol-3-one (0.312 g) as a white solid. MS (ESI+): 395.0 ([M+H]+).

後処理

  1. customThe solvent was evaporated in vacuo
  2. dissolutionthe residue was dissolved in EtOAc
  3. customThe phases were separated
  4. extractionthe aqueous phase was extracted with more EtOAc
  5. washThe combined organic phases were washed with brine
  6. dry with materialdried over sodium sulfate
  7. filtrationfiltered
  8. customto give a crude residue
  9. washFlash column chromatography over silica gel using ISCO combiflash chromatography and eluting with EtOAc/heptane

出典と根拠

ORDレコード
ord-b8c87bb180444f4490d452bd68659b72
出典データセット
uspto-grants-2010_01
特許番号
US07652057B2

反応ノート

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