Bromocyclopentane → HCID 69060133、化合物

HRID 1817501ノート

反応式

HRID 1817501 の反応式
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([C:9]([C:11]2[C:19]3[C:14](=[C:15]([C:20]([F:23])([F:22])[F:21])[CH:16]=[CH:17][CH:18]=3)[NH:13][N:12]=2)=[O:10])[CH:6]=[CH:7][CH:8]=1.[H-].[Na+].[CH:26]1(Br)[CH2:30][CH2:29][CH2:28][CH2:27]1>CN(C=O)C>[CH:26]1([N:13]2[C:14]3[C:19](=[CH:18][CH:17]=[CH:16][C:15]=3[C:20]([F:23])([F:21])[F:22])[C:11]([C:9]([C:5]3[CH:6]=[CH:7][CH:8]=[C:3]([O:2][CH3:1])[CH:4]=3)=[O:10])=[N:12]2)[CH2:30][CH2:29][CH2:28][CH2:27]1

参加物

5

反応物 3

HCID 8728BromocyclopentaneHCID 24758Sodium hydrideHCID 178490436HCID 178490436、化合物

生成物 1

HCID 69060133HCID 69060133、化合物収率 75.7%

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

反応条件

温度
50 °C

実験手順

To a solution of [3-(methoxy)phenyl](7-trifluoromethyl-1H-indazol-3-yl)methanone (0.27 g, 0.85 mmol) in 5 mL DMF was added in one portion sodium hydride (0.034 g, 0.85 mmol, 60% in oil). After the gas evolution ceased, cyclopentyl bromide (0.107 mL, 1.0 mmol) was added and the reaction was stirred at ambient to 50° C. for 24 hours. The cool reaction mixture was partitioned with EtOAc and 1 N HCl. The organic phase was washed with brine and dried (Na2SO4). Removal of the solvent in vacuo afforded the crude product which was purified by flash chromatography (silica gel, hexane/EtOAC, 9:1) to give the title compound (0.250 g) as an oil.

後処理

  1. customThe cool reaction mixture
  2. customwas partitioned with EtOAc and 1 N HCl
  3. washThe organic phase was washed with brine
  4. dry with materialdried (Na2SO4)
  5. customRemoval of the solvent in vacuo
  6. customafforded the crude product which
  7. customwas purified by flash chromatography (silica gel, hexane/EtOAC, 9:1)

出典と根拠

ORDレコード
ord-a20e288f76414338a2aa31edaa36ba28
出典データセット
uspto-grants-2009_10
特許番号
US07598286B2

反応ノート

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