Sodium hydride → 5-chloro-1-(methylsulfonyl)-1H-indole-3-carbaldehyde

HRID 1181805Notes

Reaction equation

HRID 1181805 reaction equation
[H-].[Na+].[Cl:3][C:4]1[CH:5]=[C:6]2[C:10](=[CH:11][CH:12]=1)[NH:9][CH:8]=[C:7]2[CH:13]=[O:14].[CH3:15][S:16](Cl)(=[O:18])=[O:17]>C1COCC1.CCOC(C)=O>[Cl:3][C:4]1[CH:5]=[C:6]2[C:10](=[CH:11][CH:12]=1)[N:9]([S:16]([CH3:15])(=[O:18])=[O:17])[CH:8]=[C:7]2[CH:13]=[O:14]

Participants

6

Reactant 3

HCID 24758Sodium hydrideHCID 31297Methanesulfonyl chlorideHCID 27953745-chloro-1H-indole-3-carbaldehyde

Product 1

HCID 589811545-chloro-1-(methylsulfonyl)-1H-indole-3-carbaldehydeYield 58.5%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

NaH (0.36 gm, 12.6 mmol) was added to a solution of 2.26 gm (12.6 mmol) 5-chloro-1H-indole-3-carbaldehyde in THF cooled in an ice water bath After 20 m stirring, 1.4 g (12.6 mmol) methanesulfonyl chloride was added, and the solution was warmed to room temperature with stirring overnight. The mixture was diluted with EtOAc and washed with water and brine, dried (MgSO4) and concentrated. Normal phase chromatography (CH2Cl2 followed by gradient elution to 10% EtOAc in CH2Cl2) afforded 1.9 gm of the title compound as a white solid, 1H NMR (DMSO) δ 9.75 (s, 1H), 8.0 (s, 1H), 7.9 (s, 1H), 7.5 (d, 1H), 7.1 (d, 1H), 2.3 (s, 3H).

Workup

  1. temperaturecooled in an ice water bath After 20 m
  2. stirringwith stirring overnight
  3. washwashed with water and brine
  4. dry with materialdried (MgSO4)
  5. concentrationconcentrated
  6. washNormal phase chromatography (CH2Cl2 followed by gradient elution to 10% EtOAc in CH2Cl2)

Sources & evidence

ORD record
ord-0590c90292534ce8a4ae94733556f7a1
Source dataset
uspto-grants-2007_10
Patent number
US07285558B2

Reaction notes

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