Methyl iodide → HCID 46868293, compound

HRID 506782Notes

Reaction equation

HRID 506782 reaction equation
[OH-].[K+].[CH3:3]I.[Cl:5][C:6]1[CH:11]=[CH:10][N:9]=[C:8]2[N:12]([S:28]([C:31]3[CH:36]=[CH:35][C:34]([CH3:37])=[CH:33][CH:32]=3)(=[O:30])=[O:29])[C:13]([C:15]3[C:19]4=[N:20][C:21]([O:26][CH3:27])=[C:22]([O:24][CH3:25])[CH:23]=[C:18]4[NH:17][CH:16]=3)=[CH:14][C:7]=12>CN(C=O)C.CCOC(C)=O>[Cl:5][C:6]1[CH:11]=[CH:10][N:9]=[C:8]2[N:12]([S:28]([C:31]3[CH:36]=[CH:35][C:34]([CH3:37])=[CH:33][CH:32]=3)(=[O:29])=[O:30])[C:13]([C:15]3[C:19]4=[N:20][C:21]([O:26][CH3:27])=[C:22]([O:24][CH3:25])[CH:23]=[C:18]4[N:17]([CH3:3])[CH:16]=3)=[CH:14][C:7]=12

Participants

6

Reactant 3

HCID 6328Methyl iodideHCID 14797Potassium HydroxideHCID 68467297HCID 68467297, compound

Product 1

HCID 46868293HCID 46868293, compoundYield 104.3%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

Add KOH (5.0 equiv., 21.6 mg) then MeI (5.0 equiv., 55.0 mg, 24 μL) to bisazaindole 28 (37.3 mg, 0.0772 mmol) stirred in DMF (5.0 mL) at 0° C., and stir the reaction medium at for 1.5 h. Then allow the reaction medium to return to room temperature, dilute it with EtOAc, wash it with saturated NaHCO3, dry (MgSO4) and concentrate, to obtain 29 (40 mg, 100%) as an amorphous solid: TLC (EtOAc at 40%/heptane) Rf=0.10.

Workup

  1. customto return to room temperature
  2. washwash it with saturated NaHCO3
  3. dry with materialdry (MgSO4)
  4. concentrationconcentrate

Sources & evidence

ORD record
ord-aa18d4ddaeb34ad9988aa1b885db20d6
Source dataset
uspto-grants-2010_08
Patent number
US07786114B2

Reaction notes

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