Sodium Iodide → HCID 70312831、化合物

HRID 331365ノート

反応式

HRID 331365 の反応式
[Br:1][C:2]1[C:3](=[O:20])[C:4]2[C:9]([C:10]=1[C:11]1[CH:16]=[CH:15][C:14]([F:17])=[CH:13][C:12]=1[F:18])=[CH:8][CH:7]=[C:6]([OH:19])[CH:5]=2.C([O-])([O-])=O.[K+].[K+].CS(O[CH2:32][CH2:33][CH2:34][N:35]1[CH2:40][CH2:39][N:38]([S:41]([CH3:44])(=[O:43])=[O:42])[CH2:37][CH2:36]1)(=O)=O.[Na+].[I-]>CN(C=O)C>[Br:1][C:2]1[C:3](=[O:20])[C:4]2[C:9]([C:10]=1[C:11]1[CH:16]=[CH:15][C:14]([F:17])=[CH:13][C:12]=1[F:18])=[CH:8][CH:7]=[C:6]([O:19][CH2:32][CH2:33][CH2:34][N:35]1[CH2:40][CH2:39][N:38]([S:41]([CH3:44])(=[O:43])=[O:42])[CH2:37][CH2:36]1)[CH:5]=2

参加物

6

反応物 4

HCID 5238Sodium IodideHCID 11430Potassium CarbonateHCID 703074372-Bromo-3-(2,4-difluorophenyl)-6-hydroxy-1H-inden-1-oneHCID 88266393HCID 88266393、化合物

生成物 1

HCID 70312831HCID 70312831、化合物収率 66%

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

反応条件

温度
60 °C

実験手順

To a solution of 2-bromo-3-(2,4-difluorophenyl)-6-hydroxy-1H-inden-1-one (500 mg, 1.48 mmol) obtained in Step 5 of Example 82 in DMF was added K2CO3(3 eq), 3-[4-(methylsulfonyl)piperazin-1-yl]propyl methanesulfonate (669 mg, 2.23 mmol, 1.5 eq), and NaI (0.3 eq) sequentially. The mixture was heated to 60° C. for 16 h. The reaction mixture was quenched with H2O and extracted with EtOAc. The organic layer was washed with H2O and brine, dried over MgSO4, and concentrated in vacuo. The residue was purified by silica gel column chromatography (2% MeOH/CH2Cl2) to obtain the title compound (66%).

後処理

  1. customThe reaction mixture was quenched with H2O
  2. extractionextracted with EtOAc
  3. washThe organic layer was washed with H2O and brine
  4. dry with materialdried over MgSO4
  5. concentrationconcentrated in vacuo
  6. customThe residue was purified by silica gel column chromatography (2% MeOH/CH2Cl2)

出典と根拠

ORDレコード
ord-cea1fe93e2f241bda90dff6521d838f3
出典データセット
uspto-grants-2014_11
特許番号
US08877747B2

反応ノート

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