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

HRID 1370388

Reaktionsgleichung

Reaktionsgleichung von HRID 1370388
[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

Komponenten

5

Edukt 3

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

Produkt 1

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

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

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.

Aufarbeitung

  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)

Quellen und Nachweise

ORD-Eintrag
ord-0e6da2c410904427bc9e7459cb72e2dd
Quelldatensatz
uspto-grants-2003_06
Patentnummer
US06583135B2

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