Methanesulfonyl chloride → HCID 20270203, compound

HRID 485363Notes

Reaction equation

HRID 485363 reaction equation
[OH:1][CH2:2][C:3]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[N:5]([C:12]2[CH:13]=[N:14][CH:15]=[CH:16][CH:17]=2)[CH:4]=1.[CH3:18][S:19](Cl)(=[O:21])=[O:20].C(=O)(O)[O-].[Na+]>N1C=CC=CC=1>[CH3:18][S:19]([O:1][CH2:2][C:3]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[N:5]([C:12]2[CH:13]=[N:14][CH:15]=[CH:16][CH:17]=2)[CH:4]=1)(=[O:21])=[O:20]

Participants

5

Reactant 3

HCID 31297Methanesulfonyl chlorideHCID 516892Sodium BicarbonateHCID 20270184HCID 20270184, compound

Product 1

HCID 20270203HCID 20270203, compound

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

A solution of 3.3 g of 3-hydroxymethyl-N-(3-pyridyl)indole in 25 ml of pyridine is cooled to +5° and 1.36 ml of methanesulfonyl chloride is added dropwise. After 3 hours the reaction is diluted with 75 ml of ice water and 1.5 g of sodium bicarbonate is added. Extraction with methylene chloride (3×25 ml) and drying of the extracts with sodium sulfate yields 3-(methanesulfonyloxymethyl)-N-(3-pyridyl)indole which is used directly in the next step.

Workup

  1. additionis added
  2. extractionExtraction with methylene chloride (3×25 ml)
  3. dry with materialdrying of the extracts with sodium sulfate

Sources & evidence

ORD record
ord-c94c6ffee3e34c249aa4e569ff4ffbc4
Source dataset
uspto-grants-1985_08
Patent number
US04536505

Reaction notes

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