1-Hydroxy-6-methylsulfonylindole → 6-methanesulfonyl-1H-indole

HRID 1371958Notes

Reaction equation

HRID 1371958 reaction equation
[CH3:1][S:2]([C:5]1[CH:13]=[C:12]2[C:8]([CH:9]=[CH:10][N:11]2O)=[CH:7][CH:6]=1)(=[O:4])=[O:3]>P(OCC)(OCC)OCC.C(OCC)C>[CH3:1][S:2]([C:5]1[CH:13]=[C:12]2[C:8]([CH:9]=[CH:10][NH:11]2)=[CH:7][CH:6]=1)(=[O:4])=[O:3]

Participants

4

Reactant 1

HCID 7035381-Hydroxy-6-methylsulfonylindole

Product 1

HCID 27610676-methanesulfonyl-1H-indole

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 31215Triethyl phosphiteSolvent

Conditions

Temperature
160 °C

Procedure

Dissolve 6-Methanesulfonyl-indol-1-ol (5.0 g, 23.7 mmol) in triethyl phosphite (35 ml) and heat at 160° C. for 5 hours. Cool the solution to ambient temperature and dilute with diethyl ether. Wash the ether solution with brine and water followed by drying (sodium sulfate) and reducing to residue. Crystallize the residue from warm ethyl acetate to give the title compound as colorless cubes: mp 149–152° C. MS (ACPI): m/e 196.0 (M+1). Analysis for C9H9NO2S: Calcd: C, 55.37; H, 4.65; N, 7.17; found: C, 55.14; H, 4.71; N, 7.20.

Workup

  1. temperatureCool the solution to ambient temperature
  2. washWash the ether solution with brine and water
  3. dry with materialby drying (sodium sulfate)
  4. customCrystallize the residue
  5. temperaturefrom warm ethyl acetate

Sources & evidence

ORD record
ord-d9a31402847d495ba9abaf5773d1d913
Source dataset
uspto-grants-2007_01
Patent number
US07157488B2

Reaction notes

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