Sodium hydride → 1-Cyclohexylmethyl-2-(2-furanyl)-5-methanesulfonylindole

HRID 1814072Notes

Reaction equation

HRID 1814072 reaction equation
[O:1]1[CH:5]=[CH:4][CH:3]=[C:2]1[C:6]1[NH:7][C:8]2[C:13]([CH:14]=1)=[CH:12][C:11]([S:15]([CH3:18])(=[O:17])=[O:16])=[CH:10][CH:9]=2.[H-].[Na+].[CH:21]1([CH2:27]Br)[CH2:26][CH2:25][CH2:24][CH2:23][CH2:22]1.[Cl-].[NH4+]>CN(C)C=O>[CH:21]1([CH2:27][N:7]2[C:8]3[C:13](=[CH:12][C:11]([S:15]([CH3:18])(=[O:17])=[O:16])=[CH:10][CH:9]=3)[CH:14]=[C:6]2[C:2]2[O:1][CH:5]=[CH:4][CH:3]=2)[CH2:26][CH2:25][CH2:24][CH2:23][CH2:22]1

Participants

6

Reactant 4

HCID 24758Sodium hydrideHCID 25517Ammonium ChlorideHCID 137636Cyclohexane, (bromomethyl)-HCID 225044472-(2-Furanyl)-5-methanesulfonylindole

Product 1

HCID 97988341-Cyclohexylmethyl-2-(2-furanyl)-5-methanesulfonylindoleYield 79.9%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 2-(2-furanyl)-5-methanesulfonylindole (150 mg) in N,N-dimethylformamide (6 ml), 60% sodium hydride (34.4 mg) was added at 0° C. under nitrogen atmosphere and the mixture was stirred for 15 minutes. Subsequently, cyclohexylmethyl bromide (205 mg) was added to the mixture, followed by stirring for 3 hours. After completion of the reaction, the reaction solution was poured into a saturated aqueous ammonium chloride solution, extracted with toluene, washed with a saturated aqueous NaCl solution, dried over anhydrous sodium sulfate, filtered and concentrated under reduced pressure. The resulting residue was separated using silica gel column chromatography (methanol:chloroform=1:100) to obtain 164 mg of the desired product as a pale yellow oil.

Workup

  1. stirringby stirring for 3 hours
  2. customAfter completion of the reaction
  3. extractionextracted with toluene
  4. washwashed with a saturated aqueous NaCl solution
  5. dry with materialdried over anhydrous sodium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated under reduced pressure
  8. customThe resulting residue was separated

Sources & evidence

ORD record
ord-388eec24152b40cf917b39a652775ded
Source dataset
uspto-grants-2005_04
Patent number
US06875770B2

Reaction notes

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