Water → N-methanesulfonyl-6-cyanomethylindole

HRID 1106777Notes

Reaction equation

HRID 1106777 reaction equation
[CH3:1][S:2]([N:5]1[C:13]2[C:8](=[CH:9][CH:10]=[C:11]([CH2:14]Br)[CH:12]=2)[CH:7]=[CH:6]1)(=[O:4])=[O:3].O.[C-:17]#[N:18].[Na+]>O1CCOCC1.C(OCC)(=O)C>[CH3:1][S:2]([N:5]1[C:13]2[C:8](=[CH:9][CH:10]=[C:11]([CH2:14][C:17]#[N:18])[CH:12]=2)[CH:7]=[CH:6]1)(=[O:4])=[O:3]

Participants

6

Reactant 3

HCID 962WaterHCID 8929Sodium CyanideHCID 18789641N-methanesulfonyl-6-bromomethylindole

Product 1

HCID 18789651N-methanesulfonyl-6-cyanomethylindoleYield 95.1%

Reagents, catalysts & solvents 2

HCID 8857Ethyl AcetateSolventHCID 312751,4-DioxaneSolvent

Procedure

N-methanesulfonyl-6-bromomethylindole (280 mg, 0.97 mmol, from above) was dissolved in 1 ml of dioxane. Water (1 mL) was added followed by NaCN (52 mg, 1.07 mmol). The mixture was stirred for 9 days at room temperature. The reaction mixture was diluted with 30 ml of ethyl acetate and washed with 10 ml water. The aqueous layer was washed with 30 ml ethyl acetate. The combined extracts were washed with brine, dried (Na2SO4), and concentrated. The crude product was purified by flash column chromatography (silica gel, 40% ethyl acetate/hexane) to give 216 mg of the desired N-methanesulfonyl-6-cyanomethylindole (95% yield).

Workup

  1. washwashed with 10 ml water
  2. washThe aqueous layer was washed with 30 ml ethyl acetate
  3. washThe combined extracts were washed with brine
  4. dry with materialdried (Na2SO4)
  5. concentrationconcentrated
  6. customThe crude product was purified by flash column chromatography (silica gel, 40% ethyl acetate/hexane)

Sources & evidence

ORD record
ord-51ff75a3c2284a66b6b96151affcc097
Source dataset
uspto-grants-2000_05
Patent number
US06057349

Reaction notes

Loading…