Methyl vinyl sulfone → [5-chloro-1-(2-methanesulfonyl-ethyl)-1H-indol-2-yl]-methanol

HRID 1500929Notes

Reaction equation

HRID 1500929 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[NH:7][C:6]([CH2:11][OH:12])=[CH:5]2.[CH3:13][S:14]([CH:17]=[CH2:18])(=[O:16])=[O:15]>CN(C=O)C>[Cl:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[N:7]([CH2:18][CH2:17][S:14]([CH3:13])(=[O:16])=[O:15])[C:6]([CH2:11][OH:12])=[CH:5]2

Participants

4

Reactant 2

HCID 19354Methyl vinyl sulfoneHCID 12203316(5-chloro-1H-indol-2-yl)methanol

Product 1

HCID 89924301[5-chloro-1-(2-methanesulfonyl-ethyl)-1H-indol-2-yl]-methanolYield 34.8%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of (5-chloro-1H-indol-2-yl)-methanol (3.6 g, 0.02 mol), Ce2CO3 (13 g, 0.04 mol) in 100 mL of DMF which was cooled to 0° C., was added methanesulfonyl-ethene (2.1 g, 0.02 mol) in portions. The reaction mixture was stirred at a temperature between 30° C. and 50° C. overnight. Ice-water was then added to the mixture, the precipitate was filtered and dried to give [5-chloro-1-(2-methanesulfonyl-ethyl)-1H-indol-2-yl]-methanol (2 g, yield: 34.7%).

Workup

  1. filtrationthe precipitate was filtered
  2. customdried

Sources & evidence

ORD record
ord-0544302987b74e81bdcb4f5c6eebbf87
Source dataset
uspto-grants-2015_12
Patent number
US09206191B2

Reaction notes

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