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

HRID 1356262Notes

Reaction equation

HRID 1356262 reaction equation
[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

Participants

5

Reactant 3

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

Product 1

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

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

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 12 m 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.

Workup

  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 12 m SiO2 column
  10. washeluted with a 20% to 30% EtOAc in hexane gradient)

Sources & evidence

ORD record
ord-cde2d558fd154ba1bd21ce3140517df5
Source dataset
uspto-grants-2003_07
Patent number
US06586421B2

Reaction notes

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