Water → n-Methanesufonyl-6-carbomethoxyindole

HRID 1106774Notes

Reaction equation

HRID 1106774 reaction equation
C[Si]([N-][Si](C)(C)C)(C)C.[Na+].[C:11]([C:15]1[CH:23]=[C:22]2[C:18]([CH:19]=[CH:20][NH:21]2)=[CH:17][CH:16]=1)([O:13][CH3:14])=[O:12].[CH3:24][S:25](Cl)(=[O:27])=[O:26].O>C1COCC1>[CH3:24][S:25]([N:21]1[C:22]2[C:18](=[CH:17][CH:16]=[C:15]([C:11]([O:13][CH3:14])=[O:12])[CH:23]=2)[CH:19]=[CH:20]1)(=[O:27])=[O:26]

Participants

6

Reactant 4

HCID 962WaterHCID 31297Methanesulfonyl chlorideHCID 639844Methyl indole-6-carboxylateHCID 2724254Sodium bis(trimethylsilyl)amide

Product 1

HCID 18789637n-Methanesufonyl-6-carbomethoxyindole

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

A solution of NaN(TMS)2 (1 M) in THF (11 mmol, 11 ml) was added dropwise to a -78° C solution of 6-carbomethoxyindole (876 mg, 5 mmol, prepared according to the procedure of Batcho, et al., Org. Synth. Coll. 7:34) in dry THF (10 ml). After stirring for 30 min, MeSO2Cl (1.47 mL) (Me=CH3) was added. The mixture was allowed to stir overnight then poured onto 100 ml of water. The mixture was extracted with CH2Cl2 (2×75 ml). The extracts were washed with brine, dried (Na2SO4), and the solvent was removed by rotary evaporation to give a light brown solid. The solid was purified by flash column chromatography (silica gel, 20% ethyl acetate/hexane) to give 510 mg of N-methanesulfonyl-6-carbomethoxyindole.

Workup

  1. customprepared
  2. stirringto stir overnight
  3. extractionThe mixture was extracted with CH2Cl2 (2×75 ml)
  4. washThe extracts were washed with brine
  5. dry with materialdried (Na2SO4)
  6. customthe solvent was removed by rotary evaporation
  7. customto give a light brown solid
  8. customThe solid was purified by flash column chromatography (silica gel, 20% ethyl acetate/hexane)

Sources & evidence

ORD record
ord-e290a473e3a5456782c23459c9565e39
Source dataset
uspto-grants-2000_05
Patent number
US06057349

Reaction notes

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