Triethylamine → HCID 20441667, compound

HRID 1633137Notes

Reaction equation

HRID 1633137 reaction equation
[CH3:1][S:2](Cl)(=[O:4])=[O:3].[OH:6][CH2:7][CH2:8][N:9]1[C:17]2[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=2)[C:11]([CH3:18])=[C:10]1[C:19]1[CH:20]=[N:21][CH:22]=[CH:23][CH:24]=1.C(N(CC)CC)C>C(Cl)Cl>[CH3:1][S:2]([O:6][CH2:7][CH2:8][N:9]1[C:17]2[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=2)[C:11]([CH3:18])=[C:10]1[C:19]1[CH:20]=[N:21][CH:22]=[CH:23][CH:24]=1)(=[O:4])=[O:3]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 20441682HCID 20441682, compound

Product 1

HCID 20441667HCID 20441667, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Methanesulfonyl chloride (2.70 ml) is added dropwise to a solution of 7.5 g 1-(2-hydroxyethyl)-2-(3-pyridyl)-3-methylindole and 10.34 ml of triethylamine in 150 ml of methylene chloride at -10°. This mixture is stirred at room temperature for 0.5 hour and poured into 600 ml of ice water. The resulting slurry is extracted with methylene chloride and the extract is washed with saturated NaHCO3 solution, dried over MgSO4 and evaporated in vacuo. There is obtained 1-(2-methylsulfonyloxyethyl)-2-(3-pyridyl)-3-methylindole which is used directly in the above reaction.

Workup

  1. extractionThe resulting slurry is extracted with methylene chloride
  2. washthe extract is washed with saturated NaHCO3 solution
  3. dry with materialdried over MgSO4
  4. customevaporated in vacuo

Sources & evidence

ORD record
ord-0e65165ccbc74079a30a066018bb3e56
Source dataset
uspto-grants-1984_10
Patent number
US04478842

Reaction notes

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