Methyl iodide → tert-Butyl 9-methyl-3,4-dihydro-1H-pyrido[3,4-b]indole-2(9H)-carboxylate

HRID 2301077Notes

Reaction equation

HRID 2301077 reaction equation
[H-].[Na+].[C:3]([O:7][C:8]([N:10]1[CH2:22][CH2:21][C:20]2[C:19]3[C:14](=[CH:15][CH:16]=[CH:17][CH:18]=3)[NH:13][C:12]=2[CH2:11]1)=[O:9])([CH3:6])([CH3:5])[CH3:4].[CH3:23]I>CN(C=O)C>[C:3]([O:7][C:8]([N:10]1[CH2:22][CH2:21][C:20]2[C:19]3[C:14](=[CH:15][CH:16]=[CH:17][CH:18]=3)[N:13]([CH3:23])[C:12]=2[CH2:11]1)=[O:9])([CH3:6])([CH3:4])[CH3:5]

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 18377349tert-butyl 3,4-dihydro-1H-pyrido[3,4-b]indole-2(9H)-carboxylate

Product 1

HCID 10989795tert-Butyl 9-methyl-3,4-dihydro-1H-pyrido[3,4-b]indole-2(9H)-carboxylateYield 63.5%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A 66 mg (1.65 mmol) portion of sodium hydride was added to 10 ml of DMF solution containing 300 mg (1.10 mmol) of 2-t-butoxycarbonyl-2,3,4,9-tetrahydro-1H-pyrido[3,4-b]indole and stirred at room temperature for 30 minutes, and then 103 μl (1.65 mmol) of methyl iodide were added thereto and stirred overnight at room temperature. The reaction solution was extracted with ethyl acetate and washed with water. After drying (Na2SO4), the solvent was removed by evaporation under a reduced pressure and the resulting oil was purified by a silica gel column chromatography (60 cc; elution by ethyl acetate-hexane=1:5) to obtain 200 mg of the title compound (63% in yield).

Workup

  1. stirringstirred overnight at room temperature
  2. extractionThe reaction solution was extracted with ethyl acetate
  3. washwashed with water
  4. dry with materialAfter drying (Na2SO4)
  5. customthe solvent was removed by evaporation under a reduced pressure
  6. customthe resulting oil was purified by a silica gel column chromatography (60 cc; elution by ethyl acetate-hexane=1:5)

Sources & evidence

ORD record
ord-e361cb1a865548fdbcbbe2bca783fb82
Source dataset
uspto-grants-2002_12
Patent number
US06498251B1

Reaction notes

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