Hexane → 7-Chloro-3-methanesulfonyl-1H-indole

HRID 23391Notes

Reaction equation

HRID 23391 reaction equation
CO[CH:3]=[N:4][C:5]1[C:10]([CH2:11][S:12]([CH3:15])(=[O:14])=[O:13])=[CH:9][CH:8]=[CH:7][C:6]=1[Cl:16].[OH-].[Na+].C(OCC)(=O)C.CCCCCC>CS(C)=O.[Cl-].[NH4+]>[Cl:16][C:6]1[CH:7]=[CH:8][CH:9]=[C:10]2[C:5]=1[NH:4][CH:3]=[C:11]2[S:12]([CH3:15])(=[O:14])=[O:13]

Participants

7

Reactant 4

HCID 8058HexaneHCID 8857Ethyl AcetateHCID 14798Sodium HydroxideHCID 69545940N-(2-Chloro-6-methanesulfonylmethyl-phenyl)-formimidic acid methyl ester

Product 1

HCID 225740537-Chloro-3-methanesulfonyl-1H-indole

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolventHCID 25517Ammonium ChlorideSolvent

Procedure

The crude N-(2-chloro-6-methanesulfonylmethyl-phenyl)-formimidic acid methyl ester of Step 5 was dissolved in dry DMSO (20 ml) and treated with 2 g powdered sodium hydroxide. The reaction mixture was vigorously stirred at room temperature for 1 h after which tlc (1:1 ethyl acetate:hexane, followed by 3:7) showed a single principal product, somewhat less polar than starting material. The reaction mixture was diluted with 100 ml of a 10% ammonium chloride solution and extracted with ethyl acetate, washed twice with water, and the crude solution was passed through a short silica gel column and eluted with ethyl acetate to remove colored impurities. The resulting crystalline 7-chloro-3-methanesulfonyl-1H-indole weighed 2.21 g.

Workup

  1. additiontreated with 2 g
  2. extractionextracted with ethyl acetate
  3. washwashed twice with water
  4. washeluted with ethyl acetate
  5. customto remove colored impurities

Sources & evidence

ORD record
ord-05cd4ea97aa64d2ea1a2cc382afbdc4f
Source dataset
uspto-grants-2005_02
Patent number
US06852726B2

Reaction notes

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