Sodium hydride → (6-Chloro-1-methanesulfonyl-1H-indol-3-yl)-[4-(2-methoxy-phenyl)-piperidin-1-yl]-methanone

HRID 505156Notes

Reaction equation

HRID 505156 reaction equation
[Cl:1][C:2]1[CH:10]=[C:9]2[C:5]([C:6]([C:11]([N:13]3[CH2:18][CH2:17][CH:16]([C:19]4[CH:24]=[CH:23][CH:22]=[CH:21][C:20]=4[O:25][CH3:26])[CH2:15][CH2:14]3)=[O:12])=[CH:7][NH:8]2)=[CH:4][CH:3]=1.[H-].[Na+].[CH3:29][S:30](Cl)(=[O:32])=[O:31]>CN(C)C=O>[Cl:1][C:2]1[CH:10]=[C:9]2[C:5]([C:6]([C:11]([N:13]3[CH2:18][CH2:17][CH:16]([C:19]4[CH:24]=[CH:23][CH:22]=[CH:21][C:20]=4[O:25][CH3:26])[CH2:15][CH2:14]3)=[O:12])=[CH:7][N:8]2[S:30]([CH3:29])(=[O:32])=[O:31])=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 31297Methanesulfonyl chlorideHCID 59429632(6-Chloro-1H-indol-3-yl)[4-(2-methoxyphenyl)piperidin-1-yl]methanone

Product 1

HCID 59429613(6-Chloro-1-methanesulfonyl-1H-indol-3-yl)-[4-(2-methoxy-phenyl)-piperidin-1-yl]-methanoneYield 17.4%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 0.035 g (0.09 mmol) (6-chloro-1H-indol-3-yl)-[4-(2-methoxy-phenyl)-piperidin-1-yl]-methanone in 2 ml N,N-dimethylformamide were added 0.005 g (0.10 mmol) sodium hydride (50% in oil). After 45′, 0.008 ml (0.10 mmol) methanesulfonyl chloride were added. The reaction mixture was quenched with water after 3 h and extracted with ethyl acetate (2×50 ml). The combined organic layers were washed with water (2×30 ml) and brine (1×30), dried over sodium sulfate and concentrated to dryness. The residue was chromatographed (loaded as a solution in toluene; Flashpac 5 g; n-heptane/ethyl acetate 100:0→75:25) to give the title compound (0.007 g; 17%) as a light yellow solid.

Workup

  1. customThe reaction mixture was quenched with water after 3 h
  2. extractionextracted with ethyl acetate (2×50 ml)
  3. washThe combined organic layers were washed with water (2×30 ml) and brine (1×30)
  4. dry with materialdried over sodium sulfate
  5. concentrationconcentrated to dryness
  6. customThe residue was chromatographed (

Sources & evidence

ORD record
ord-3c49f3e008544c3a872a1dc90f0b460b
Source dataset
uspto-grants-2010_08
Patent number
US07781436B2

Reaction notes

Loading…