Aziridine → HCID 11504035、化合物

HRID 1868422

反応式

HRID 1868422 の反応式
[C:1]1([C:7]2[C:15]3[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=3)[NH:9][CH:8]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[H-].[Na+].[H][H].[F:20][C:21]([F:38])([F:37])[CH:22]1[CH2:24][N:23]1[S:25]([C:28]1[C:33]([CH3:34])=[CH:32][C:31]([CH3:35])=[CH:30][C:29]=1[CH3:36])(=[O:27])=[O:26].N1CC1>CN(C=O)C>[CH3:36][C:29]1[CH:30]=[C:31]([CH3:35])[CH:32]=[C:33]([CH3:34])[C:28]=1[S:25]([NH:23][CH:22]([CH2:24][N:9]1[C:10]2[C:15](=[CH:14][CH:13]=[CH:12][CH:11]=2)[C:7]([C:1]2[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=2)=[CH:8]1)[C:21]([F:38])([F:20])[F:37])(=[O:26])=[O:27]

参加物

7

反応物 5

HCID 9033AziridineHCID 24758Sodium hydrideHCID 965023-PhenylindoleHCID 574740362-Trifluoromethyl-1-(2,4,6-trimethylbenzenesulfonyl)aziridineHCID 178418361HCID 178418361、化合物

生成物 1

HCID 11504035HCID 11504035、化合物収率 72.3%

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

実験手順

To a solution of 48 mg (0.25 mmol) of 3-phenyl-1H-indole in 3 mL of DMF was added 28 mg (0.7 mmol) of 60% sodium hydride in mineral oil. The mixture stirred until hydrogen evolution ceased and then 73 mg (0.25 mmol) of 2-trifluoromethyl-1-(2,4,6-trimethylbenzenesulfonyl)aziridine was added. The reaction was monitored by TLC (20% EtOAc-hexanes and 50% hexanes-CH2Cl2) indicating starting aziridine was consumed. After 30 minutes, the mixture was quenched with 7 mL of saturated aqueous ammonium chloride solution and extracted with three 7 mL portions of ethyl acetate. The combined organic layers were washed with three 7 mL portions of saturated aqueous ammonium chloride solution and three 7 mL portions of brine, dried over magnesium sulfate, filtered, and concentrated in vacuo. The residue was triturated with ether to afford 88 mg (72%) of the title compound. MS: m/z 487.59 (M+1).

後処理

  1. customwas consumed
  2. customthe mixture was quenched with 7 mL of saturated aqueous ammonium chloride solution
  3. extractionextracted with three 7 mL portions of ethyl acetate
  4. washThe combined organic layers were washed with three 7 mL portions of saturated aqueous ammonium chloride solution and three 7 mL portions of brine
  5. dry with materialdried over magnesium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo
  8. customThe residue was triturated with ether

出典と根拠

ORDレコード
ord-aa2b08c421de4568a875b676811756a6
出典データセット
uspto-grants-2009_12
特許番号
US07635711B2

関連ノート

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