Methyl vinyl sulfone → 5-Bromo-2-(2-(methylsulfonyl)ethyl)-1,2,3,4-tetrahydroisoquinoline

HRID 1890744Notes

Reaction equation

HRID 1890744 reaction equation
[Br:1][C:2]1[CH:11]=[CH:10][CH:9]=[C:8]2[C:3]=1[CH2:4][CH2:5][NH:6][CH2:7]2.[CH3:12][S:13]([CH:16]=[CH2:17])(=[O:15])=[O:14]>ClCCl>[Br:1][C:2]1[CH:11]=[CH:10][CH:9]=[C:8]2[C:3]=1[CH2:4][CH2:5][N:6]([CH2:17][CH2:16][S:13]([CH3:12])(=[O:15])=[O:14])[CH2:7]2

Participants

4

Reactant 2

HCID 19354Methyl vinyl sulfoneHCID 128231995-Bromo-1,2,3,4-tetrahydroisoquinoline

Product 1

HCID 583180515-Bromo-2-(2-(methylsulfonyl)ethyl)-1,2,3,4-tetrahydroisoquinoline

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
35 °C

Procedure

A mixture containing 5-bromo-1,2,3,4-tetrahydroisoquinoline (212 mg, 1 mmol) and methylsulfonylethene (106 mg, 1 mmol) in dichloromethane is stirred at 35° C. for 14 hours. The solution is concentrated to afford 5-bromo-2-(2-(methylsulfonyl)ethyl)-1,2,3,4-tetrahydroisoquinoline as a brown oil (LC-MS m/z: 318.1 (M+1)) which is used without further purification in the next step.

Workup

  1. concentrationThe solution is concentrated

Sources & evidence

ORD record
ord-51460749f2874f52997f63e5cbb855a0
Source dataset
uspto-grants-2013_08
Patent number
US08507491B2

Reaction notes

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