Sodium hydride → HCID 22615760, compound

HRID 366500Notes

Reaction equation

HRID 366500 reaction equation
[H-].[Na+].[CH2:3]([O:10][C:11]([N:13]1[CH2:18][CH2:17][CH:16]([C:19]2[C:27]3[C:22](=[CH:23][CH:24]=[C:25]([C:28]#[N:29])[CH:26]=3)[NH:21][CH:20]=2)[CH2:15][CH2:14]1)=[O:12])[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1.[CH3:30][S:31](Cl)(=[O:33])=[O:32]>CN(C)C=O.C(OCC)(=O)C>[CH2:3]([O:10][C:11]([N:13]1[CH2:14][CH2:15][CH:16]([C:19]2[C:27]3[C:22](=[CH:23][CH:24]=[C:25]([C:28]#[N:29])[CH:26]=3)[N:21]([S:31]([CH3:30])(=[O:33])=[O:32])[CH:20]=2)[CH2:17][CH2:18]1)=[O:12])[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1

Participants

6

Reactant 3

HCID 24758Sodium hydrideHCID 31297Methanesulfonyl chlorideHCID 22615744HCID 22615744, compound

Product 1

HCID 22615760HCID 22615760, compoundYield 54%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

Sodium hydride (115 mg, 4.8 mmol) was added to a solution of 1-benzyloxycarbonyl-4-(5-cyanoindol-3-yl)piperidine (1.5 g, 4.17 mmol) [prepared as described in Step 1 above] in dimethylformamide (12 ml) at 0° C. After 30 min., methanesulfonyl chloride (0.81 ml, 10.43 mmol) was added and after stirring for 2.5 h the reaction mixture was allowed to warm to RT over 1 h. The reaction mixture was diluted with ethyl acetate (100 ml) and washed with water, brine and dried over MgSO4. The organics were evaporated in vacuo and the residue was chromatographed (PILC, SiO2, 40% ethyl acetateihexanes) to give 1-benzyloxycarbonyl-4-(5-cyano-1-methanesulfonylindol-3-yl)piperidine (54%) as a pale yellow oil.

Workup

  1. washwashed with water, brine
  2. dry with materialdried over MgSO4
  3. customThe organics were evaporated in vacuo
  4. customthe residue was chromatographed (PILC, SiO2, 40% ethyl acetateihexanes)

Sources & evidence

ORD record
ord-24fa95e0f9214beea38500b06eb70c4c
Source dataset
uspto-grants-2000_10
Patent number
US06130220

Reaction notes

Loading…