Potassium Cyanide → HCID 22262947, compound

HRID 489727Notes

Reaction equation

HRID 489727 reaction equation
[C-:1]#[N:2].[K+].[CH3:4][S:5]([N:8]1[C:16]2[C:11](=[CH:12][C:13]([O:17][CH3:18])=[CH:14][CH:15]=2)[C:10]([CH2:19]O)=[C:9]1[CH3:21])(=[O:7])=[O:6]>CS(C)=O.O1CCCC1>[CH3:4][S:5]([N:8]1[C:16]2[C:11](=[CH:12][C:13]([O:17][CH3:18])=[CH:14][CH:15]=2)[C:10]([CH2:19][C:1]#[N:2])=[C:9]1[CH3:21])(=[O:7])=[O:6]

Participants

5

Reactant 2

HCID 9032Potassium CyanideHCID 22262935HCID 22262935, compound

Product 1

HCID 22262947HCID 22262947, compound

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolventHCID 8028TetrahydrofuranSolvent2×

Procedure

To a suspension of potassium cyanide (3.0 g, 46.1 mmol) in methyl sulfoxide (16 ml) and tetrahydrofuran (4 ml) at 0° C. was added a solution of (1-methanesulfonyl-5-methoxy-2-methyl-1H-indol-3-yl)-methanol (0.26 g,) in tetrahydrofuran (20 ml) at 0° C. The reaction mixture was stirred at room temperature for 8 hours and then kept at 4° C. for 72 hours. The mixture was partitioned between ethyl acetate and water, and the organic extract was washed with brine, dried (anhydrous sodium sulfate) and concentrated under reduced pressure. The residue was purified by flash column chromatography over silica gel eluting with 50 to 70% ethyl acetate in hexane) to give (1-methanesulfonyl-5-methoxy-2-methyl-1H-indol-3-yl)-acetonitrile as a white solid, (0.2 g, 13% in 2 steps). 1H NMR (CDCl3) δ: 2.58 (s, 3H), 3.03 (s, 3H), 3.71 (s, 2H), 3.88 (s, 3H), 6.93-6.99 (m, 2H), 7.91 (dd, 1H, J=8.9 Hz, 0.6 Hz).

Workup

  1. waitkept at 4° C. for 72 hours
  2. customThe mixture was partitioned between ethyl acetate and water
  3. extractionthe organic extract
  4. washwas washed with brine
  5. dry with materialdried (anhydrous sodium sulfate)
  6. concentrationconcentrated under reduced pressure
  7. customThe residue was purified by flash column chromatography over silica gel eluting with 50 to 70% ethyl acetate in hexane)

Sources & evidence

ORD record
ord-f11c2671305b4fca9829ea93d534121d
Source dataset
uspto-grants-2005_12
Patent number
US06979696B2

Reaction notes

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