Benzenesulfonyl chloride → HCID 15951554, compound

HRID 1865923Notes

Reaction equation

HRID 1865923 reaction equation
[CH3:1][C:2]1[NH:3][C:4]2[C:9]([C:10]=1[C:11]([N:13]1[CH2:18][CH2:17][C:16]3([C:22]4[CH:23]=[CH:24][CH:25]=[CH:26][C:21]=4[CH2:20][O:19]3)[CH2:15][CH2:14]1)=[O:12])=[CH:8][CH:7]=[CH:6][CH:5]=2.[H-].[Na+].[C:29]1([S:35](Cl)(=[O:37])=[O:36])[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=1>CN(C=O)C>[CH3:1][C:2]1[N:3]([S:35]([C:29]2[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=2)(=[O:37])=[O:36])[C:4]2[C:9]([C:10]=1[C:11]([N:13]1[CH2:14][CH2:15][C:16]3([C:22]4[CH:23]=[CH:24][CH:25]=[CH:26][C:21]=4[CH2:20][O:19]3)[CH2:17][CH2:18]1)=[O:12])=[CH:8][CH:7]=[CH:6][CH:5]=2

Participants

5

Reactant 3

HCID 7369Benzenesulfonyl chlorideHCID 24758Sodium hydrideHCID 15951552HCID 15951552, compound

Product 1

HCID 15951554HCID 15951554, compoundYield 84.1%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a stirred solution of 40 mg (0.11 mmol) of 1′-[(2-methyl-1H-indol-3-yl)carbonyl]-3H-spiro[2-benzofuran-1,4′-piperidine] (the preparation of which has been described in example 43) in 3 ml DMF was added 5 mg (0.11 mmol) NaH (60% in oil). The mixture was stirred at RT for 30 min. and then 24 mg (0.14 mmol) of benzenesulfonyl chloride was added. The mixture was stirred an additional hour and then poured onto water and extracted with ethyl acetate. The combined organic phases were dried over Na2SO4 and concentrated in vacuo. Re-crystallization in Et2O afforded 45 mg (80%) of 1′-{[2-methyl-1-(phenylsulfonyl)-1H-indol-3-yl]carbonyl}-3H-spiro[2-benzofuran-1,4′-piperidine] as white crystals. ES-MS m/e (%): 487.4 (M+H+).

Workup

  1. stirringThe mixture was stirred an additional hour
  2. additionpoured onto water
  3. extractionextracted with ethyl acetate
  4. dry with materialThe combined organic phases were dried over Na2SO4
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-1dad9a069e1c460ba5d8bcc0b405e988
Source dataset
uspto-grants-2009_12
Patent number
US07629353B2

Reaction notes

Loading…