Methyl iodide → 1-Methyl-6-methylsulfonyl-indole

HRID 1009008

Reaction equation

HRID 1009008 reaction equation
[H-].[Na+].[CH3:3][S:4]([C:7]1[CH:15]=[C:14]2[C:10]([CH:11]=[CH:12][NH:13]2)=[CH:9][CH:8]=1)(=[O:6])=[O:5].[H][H].[CH3:18]I>>[CH3:3][S:4]([C:7]1[CH:15]=[C:14]2[C:10]([CH:11]=[CH:12][N:13]2[CH3:18])=[CH:9][CH:8]=1)(=[O:6])=[O:5]

Participants

5

Reactant 4

HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 27610676-methanesulfonyl-1H-indoleHCID 178418361HCID 178418361, compound

Product 1

HCID 673057701-Methyl-6-methylsulfonyl-indole

Procedure

To a slurry of sodium hydride (60% in mineral oil, 0.90 g, 23 mmol) was added in portions 6-(methylsulfonyl)-1H-indole (4.0 g, 20 mmol) over 5 minutes at 5-10° C. The reaction mixture was stirred at rt for 1 h until hydrogen evolution ceased, and methyl iodide was added dropwise over 5 minutes at 10-20° C. The mixture was stirred at rt for 1 h, quenched with ice/water, and extracted with tert-butylmethyl ether. The organics were washed, dried and concentrated. The residue was crystallized from ether/hexane to yield the desired compound (3.8 g) as a yellowish solid. MS (ISP): m/e 210.1 (M+H)+

Workup

  1. customquenched with ice/water
  2. extractionextracted with tert-butylmethyl ether
  3. washThe organics were washed
  4. customdried
  5. concentrationconcentrated
  6. customThe residue was crystallized from ether/hexane

Sources & evidence

ORD record
ord-9d5b83a1bc4549048bad5a5140fbae72
Source dataset
uspto-grants-2011_07
Patent number
US07973051B2

Linked notes

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