Sodium hydride → tert-butyl 6-[2-(phenylsulfinyl)ethyl]-1,4,5,6-tetrahydroazepino[4,5-b]indole-3(2H)-carboxylate

HRID 1370388

反応式

HRID 1370388 の反応式
[CH2:1]1[C:14]2[C:13]3[CH:12]=[CH:11][CH:10]=[CH:9][C:8]=3[NH:7][C:6]=2[CH2:5][CH2:4][N:3]([C:15]([O:17][C:18]([CH3:21])([CH3:20])[CH3:19])=[O:16])[CH2:2]1.[C:22]1([S:28]([CH2:30][CH2:31]Cl)=[O:29])[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1.[H-].[Na+]>CN(C=O)C>[C:22]1([S:28]([CH2:30][CH2:31][N:7]2[C:8]3[CH:9]=[CH:10][CH:11]=[CH:12][C:13]=3[C:14]3[CH2:1][CH2:2][N:3]([C:15]([O:17][C:18]([CH3:21])([CH3:20])[CH3:19])=[O:16])[CH2:4][CH2:5][C:6]2=3)=[O:29])[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1

参加物

5

反応物 3

HCID 24758Sodium hydrideHCID 99293((2-Chloroethyl)sulphinyl)benzeneHCID 22396759tert-butyl 1,4,5,6-tetrahydroazepino[4,5-b]indole-3(2H)-carboxylate

生成物 1

HCID 22396668tert-butyl 6-[2-(phenylsulfinyl)ethyl]-1,4,5,6-tetrahydroazepino[4,5-b]indole-3(2H)-carboxylate

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

実験手順

tert-Butyl 1,4,5,6-tetrahydroazepino[4,5-b]indole-3(2H)-carboxylate (0.170 g, 0.594 mmol) and 2-chloroethyl phenyl sulfoxide (0.225 g, 1.20 mmol, 2.0 equiv.) was dissolved in DMF (10 mL) at rt. NaH (0.100 mg, 2.5 mmol, 4.21 equiv., 60% dispersion) was added, then the reaction mixture was stirred for 3 h. The reaction was quenched with a saturated aqueous NH4Cl solution and partitioned between water and CH2Cl2. The aqueous layer was extracted with CH2Cl2 (3×). The combined organic layers were concentrated and the residue was dissolved in EtOAc, dried over MgSO4, filtered, and concentrated. The crude product was chromatographed (Biotage 12m SiO2 column, eluted with a 20% to 30% EtOAc in hexane gradient) to give tert-butyl 6-[2-(phenylsulfinyl)ethyl]-1,4,5,6-tetrahydroazepino[4,5-b]indole-3(2H)-carboxylate.

後処理

  1. customThe reaction was quenched with a saturated aqueous NH4Cl solution
  2. custompartitioned between water and CH2Cl2
  3. extractionThe aqueous layer was extracted with CH2Cl2 (3×)
  4. concentrationThe combined organic layers were concentrated
  5. dissolutionthe residue was dissolved in EtOAc
  6. dry with materialdried over MgSO4
  7. filtrationfiltered
  8. concentrationconcentrated
  9. customThe crude product was chromatographed (Biotage 12m SiO2 column
  10. washeluted with a 20% to 30% EtOAc in hexane gradient)

出典と根拠

ORDレコード
ord-0e6da2c410904427bc9e7459cb72e2dd
出典データセット
uspto-grants-2003_06
特許番号
US06583135B2

関連ノート

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