Ethyl Bromide → 3-(1,4-Dioxa-spiro[4,5]dec-8-yl)-5-cyano-1-ethyl-indole

HRID 992028Notes

Reaction equation

HRID 992028 reaction equation
[H-].[Na+].[O:3]1[C:7]2([CH2:12][CH2:11][CH: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)[CH2:9][CH2:8]2)[O:6][CH2:5][CH2:4]1.[CH2:24](Br)[CH3:25]>CN(C)C=O>[O:6]1[C:7]2([CH2:12][CH2:11][CH:10]([C:13]3[C:21]4[C:16](=[CH:17][CH:18]=[C:19]([C:22]#[N:23])[CH:20]=4)[N:15]([CH2:24][CH3:25])[CH:14]=3)[CH2:9][CH2:8]2)[O:3][CH2:4][CH2:5]1

Participants

5

Reactant 3

HCID 6332Ethyl BromideHCID 24758Sodium hydrideHCID 155219733-(1,4-Dioxa-spiro[4,5]dec-8-yl)-5-cyano-1H-indole

Product 1

HCID 184140623-(1,4-Dioxa-spiro[4,5]dec-8-yl)-5-cyano-1-ethyl-indoleYield 69%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a suspension of sodium hydride (60%, 1.63 g, 0.068 mol) in anhydrous N,N-dimethylformamide (150 ml) was added 3-(1,4-dioxa-spiro[4,5]dec-8-yl)-5-cyano-1H-indole (9.0 g, 0.032 mol) at room temperature. The mixture was stirred for 30 minutes at room temperature then ethylbromide (14.6 g, 0.13 mol) was added at room temperature. The reaction was allowed to stir for overnight, 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 (hexanes) afforded 5.5 g (69%) of product as a white solid: mp 124-126° C.

Workup

  1. stirringto stir for overnight
  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-242ba5d71ce64340b890440154a00de0
Source dataset
uspto-grants-2002_10
Patent number
US06465482B2

Reaction notes

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