Benzenesulfonyl chloride → HCID 11133773, compound

HRID 635379Notes

Reaction equation

HRID 635379 reaction equation
[C:1]([O:5][C:6]([NH:8][CH2:9][CH2:10][C:11]1[C:19]2[C:14](=[CH:15][CH:16]=[C:17]([O:20][CH3:21])[CH:18]=2)[NH:13][CH:12]=1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[C:22]1([S:28](Cl)(=[O:30])=[O:29])[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1>ClCCl.[OH-].[Na+].S([O-])(O)(=O)=O.C([N+](CCCC)(CCCC)CCCC)CCC.C(OCC)C>[C:22]1([S:28]([N:13]2[C:14]3[C:19](=[CH:18][C:17]([O:20][CH3:21])=[CH:16][CH:15]=3)[C:11]([CH2:10][CH2:9][NH:8][C:6]([O:5][C:1]([CH3:3])([CH3:4])[CH3:2])=[O:7])=[CH:12]2)(=[O:30])=[O:29])[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1

Participants

7

Reactant 2

HCID 7369Benzenesulfonyl chlorideHCID 21258552HCID 21258552, compound

Product 1

HCID 11133773HCID 11133773, compoundYield 95%

Reagents, catalysts & solvents 4

HCID 94433Tetrabutylammonium hydrogen sulfateCatalystHCID 3283Diethyl EtherSolventHCID 6344DichloromethaneSolventHCID 14798Sodium HydroxideSolvent

Procedure

To a stirred two-phase mixture of a solution of the above 3-[2-(tert-butyloxycarbonylamino)ethyl]-5-methoxy-1H-indole in dichloromethane (200 ml) and 50% aqueous sodium hydroxide (50 ml) was added tetrabutylammonium hydrogen sulphate (611 mg, 1.8 mmol) and the mixture was stirred for 10 minutes. Benzenesulphonyl chloride (3.52 ml, 27.6 mmol) was added dropwise uia syringe and the mixture was vigorously stirred for 30 minutes. The mixture was diluted with diethyl ether (500 ml), washed with water (100 ml), brine (2×70 ml), dried (MgSO4) and concentrated. Flash chromatography of the residue (silica gel, dichloromethane-diethyl ether, 90:10) followed by trituration with hexane-diethyl ether (10;1; 100 ml) afforded 1-(benzenesulphonyl)-3-[2-(tert-butyloxycarbonylamino)ethyl]-5-methoxy-1H-indole (7.55 g, 95%) as a white solid; δH (360 MHz, CDCl3) 7.88 (1H, d, J=8.8 Hz), 7.84-7.80 (2H, m), 7.54-7.48 (1H, m), 7.45-7.38 (2H, m), 7.32 (1H, s), 6.96-6.90 (2H, m), 4.55 (1H, br s), 3.82 (3H, s), 3.44-3.36 (2H, m), 2.82 (2H, t, J=6.8 Hz), 1.45 (9H, s).

Workup

  1. stirringthe mixture was vigorously stirred for 30 minutes
  2. washwashed with water (100 ml), brine (2×70 ml)
  3. dry with materialdried (MgSO4)
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-864db666fbb14b40a4663b72f4d0fb26
Source dataset
uspto-grants-2001_02
Patent number
US06187805B1

Reaction notes

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