Iodoethane → HCID 22185238, compound

HRID 1168727Notes

Reaction equation

HRID 1168727 reaction equation
[Cl:1][C:2]1[C:14]([OH:15])=[C:13]2[C:5]([C:6]3[CH:7]=[CH:8][N:9]=[CH:10][C:11]=3[N:12]2[Cl:16])=[CH:4][CH:3]=1.C([O-])([O-])=O.[K+].[K+].[CH2:23](I)[CH3:24]>CC(C)=O>[Cl:1][C:2]1[C:14]([O:15][CH2:23][CH3:24])=[C:13]2[C:5]([C:6]3[CH:7]=[CH:8][N:9]=[CH:10][C:11]=3[N:12]2[Cl:16])=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 6340IodoethaneHCID 11430Potassium CarbonateHCID 22185280HCID 22185280, compound

Product 1

HCID 22185238HCID 22185238, compoundYield 20.3%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

A mixture of the product of example 38 (35 mg, 0.14 mmol), K2CO3 (100 mg), and ethyl iodide (0.014 ml, 0.17 mmol) in acetone (5 ml) was stirred in a closed reaction tube at RT for 3 days. After concentrating the reaction, the residue was partitioned in ethyl acetate and water. The organic layer was dried (MgSO4) and concentrated to give crude product. The crude product was chromatographed (5% methanol in chloroform) on silica gel to give 8 mg of 7,9-dichloro-8-ethoxy-β-carboline.

Workup

  1. concentrationAfter concentrating
  2. customthe reaction
  3. customthe residue was partitioned in ethyl acetate
  4. dry with materialThe organic layer was dried (MgSO4)
  5. concentrationconcentrated
  6. customto give crude product
  7. customThe crude product was chromatographed (5% methanol in chloroform) on silica gel

Sources & evidence

ORD record
ord-c846625318c9447b9534dad27bba1dee
Source dataset
uspto-grants-2003_09
Patent number
US06627637B2

Reaction notes

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