Iodoethane → HCID 21087571, compound

HRID 348528Notes

Reaction equation

HRID 348528 reaction equation
[CH2:1]1[C:6]2[NH:7][C:8]3[C:9]([C:14]([O:16][CH2:17]C)=[O:15])=[CH:10][CH2:11][CH2:12][C:13]=3[C:5]=2[CH:4]=[CH:3][NH:2]1.[H-].[Na+].[CH2:21](I)[CH3:22]>CN(C=O)C>[CH2:21]([CH:12]1[CH2:11][CH:10]=[C:9]([C:14]([O:16][CH3:17])=[O:15])[C:8]2[NH:7][C:6]3[CH2:1][NH:2][CH:3]=[CH:4][C:5]=3[C:13]1=2)[CH3:22]

Participants

5

Reactant 3

HCID 6340IodoethaneHCID 24758Sodium hydrideHCID 21087566HCID 21087566, compound

Product 1

HCID 21087571HCID 21087571, compoundYield 72.2%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
0 °C

Procedure

Ethyl 1,2,5,6-tetrahydropyrido[3,4-b]indole-8-carboxylate (0.62 g, 2.68 mmol) was dissolved in DMF (10 mL) and cooled to 0° C. Sodium hydride (60% suspension in mineral oil, 0.16 g, 6.7 mmol) was added and the mixture stirred for 45 min prior to addition of ethyl iodide (0.50 g, 3.22 mmol). The mixture was stirred for 15 hours, then quenched with water and extracted with ethyl acetate. The organic layer was then removed and the crude was redissolved in acetonitrile and then washed with hexane to remove the mineral oil. The acetonitrile layer was evaporated to afford 0.5 g of title compound.

Workup

  1. stirringThe mixture was stirred for 15 hours
  2. customquenched with water
  3. extractionextracted with ethyl acetate
  4. customThe organic layer was then removed
  5. dissolutionthe crude was redissolved in acetonitrile
  6. washwashed with hexane
  7. customto remove the mineral oil
  8. customThe acetonitrile layer was evaporated

Sources & evidence

ORD record
ord-d99921ec309f4ad887a5bf3c8b8a537b
Source dataset
uspto-grants-2007_02
Patent number
US07176322B2

Reaction notes

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