Methyl iodide → 3-(1,4-Dioxa-spiro[4,5]dec-7-en-8-yl)-5-cyano-1-methyl-indole

HRID 992027Notes

Reaction equation

HRID 992027 reaction equation
[H-].[Na+].[O:3]1[C:7]2([CH2:12][CH2:11][C:10]([C:13]3[C:21]4[C:16](=[CH:17][CH:18]=[C:19]([C:22]#[N:23])[CH:20]=4)[NH:15][CH:14]=3)=[CH:9][CH2:8]2)[O:6][CH2:5][CH2:4]1.[CH3:24]I>CN(C)C=O>[O:6]1[C:7]2([CH2:12][CH2:11][C:10]([C:13]3[C:21]4[C:16](=[CH:17][CH:18]=[C:19]([C:22]#[N:23])[CH:20]=4)[N:15]([CH3:24])[CH:14]=3)=[CH:9][CH2:8]2)[O:3][CH2:4][CH2:5]1

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 155219723-(1,4-Dioxaspiro[4.5]dec-7-EN-8-YL)-1H-indole-5-carbonitrile

Product 1

HCID 184141023-(1,4-Dioxa-spiro[4,5]dec-7-en-8-yl)-5-cyano-1-methyl-indoleYield 24.7%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a suspension of sodium hydride (60%, 1.74 g, 0.073 mol) in anhydrous N,N-dimethylformamide (100 ml) was added 3-(1,4-dioxa-spiro[4,5]dec-7-en-8-yl)-5-cyano-1H-indole (9.9 g, 0.035 mol) at room temperature. The mixture was stirred for 30 minutes at room temperature, then methyl iodide (9 ml, 0.14 mol) was added at room temperature. The reaction was allowed to stir for 1 hour, then quenched with water (50 ml). The mixture was extracted with methylene chloride (3×150 ml) and water (3×150 ml). The organic layer was dried over anhydrous magnesium sulfate and filtered. The solvent was removed under vacuum. Chromatography (5% methanol-methylene chloride) afforded 2.54 g (24%) of product as a light yellow solid: mp 65-67° C.

Workup

  1. stirringto stir for 1 hour
  2. customquenched with water (50 ml)
  3. extractionThe mixture was extracted with methylene chloride (3×150 ml) and water (3×150 ml)
  4. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  5. filtrationfiltered
  6. customThe solvent was removed under vacuum

Sources & evidence

ORD record
ord-4e9759686e8241e29fb3c567e7f0f409
Source dataset
uspto-grants-2002_10
Patent number
US06465482B2

Reaction notes

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