Iodoethane → HCID 22185269, compound

HRID 1168726Notes

Reaction equation

HRID 1168726 reaction equation
O[C:2]1[C:14]2[C:6](=[C:7]3[C:12]([N:13]=2)=[CH:11][N:10]([CH3:15])[CH:9]=[CH:8]3)[CH:5]=[CH:4][CH:3]=1.[C:16]([O-:19])([O-])=O.[K+].[K+].[CH2:22](I)C>CN(C=O)C>[CH2:16]([O:19][C:3]1[CH:4]=[CH:5][C:6]2[C:14]([CH:2]=1)=[N:13][C:12]1[C:7]=2[CH:8]=[CH:9][N:10]([CH3:15])[CH:11]=1)[CH3:22]

Participants

5

Reactant 3

HCID 6340IodoethaneHCID 11430Potassium CarbonateHCID 22185283HCID 22185283, compound

Product 1

HCID 22185269HCID 22185269, compoundYield 29.5%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution of the product from example 23 (60 mg, 0.30 mmol) in DMF (3 ml) was treated with K2CO3 (100 mg) and ethyl iodide (0,029 ml, 0.36 mmol). After stirring at RT for 18 h, the reaction was partitioned in EtOAc and water. The organic layer was dried (brine; MgSO4) and then concentrated. The residue was chromatographed (1:1 hexane-acetone) on silica gel to give 20 mg of 7-ethoxy-2-methyl-β-carboline.

Workup

  1. customthe reaction was partitioned in EtOAc
  2. dry with materialThe organic layer was dried (brine; MgSO4)
  3. concentrationconcentrated
  4. customThe residue was chromatographed (1:1 hexane-acetone) on silica gel

Sources & evidence

ORD record
ord-ae40343ddc024d268c7adbd2a342aa90
Source dataset
uspto-grants-2003_09
Patent number
US06627637B2

Reaction notes

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