2-Methylindole → Sbb044946

HRID 1733854Notes

Reaction equation

HRID 1733854 reaction equation
[CH3:1][C:2]1[NH:3][C:4]2[C:9]([CH:10]=1)=[CH:8][CH:7]=[CH:6][CH:5]=2.C[Mg+].[Br-].Br[CH2:15][C:16]([O:18][CH3:19])=[O:17].C([O-])(O)=O.[Na+]>C1COCC1.[Cl-].[Cl-].[Zn+2]>[CH3:1][C:2]1[NH:3][C:4]2[C:9]([C:10]=1[CH2:15][C:16]([O:18][CH3:19])=[O:17])=[CH:8][CH:7]=[CH:6][CH:5]=2

Participants

7

Reactant 4

HCID 72242-MethylindoleHCID 60984Methyl bromoacetateHCID 516892Sodium BicarbonateHCID 178418689HCID 178418689, compound

Product 1

HCID 10774509Sbb044946Yield 43.1%

Reagents, catalysts & solvents 2

HCID 3007855ZincchlorideCatalystHCID 8028TetrahydrofuranSolvent2×

Procedure

To 2-methyl indole (1.69 g; 12.9 mmol) in 10 mL of THF at 0° C. was added MeMgBr 1.4M (12.9 mmol). After 30 min at 0° C. ZnCl2 1M (12.9 mL; 12.9 mmol) in THF was added and the reaction stirred for an other 30 min at r.t. Methyl bromoacetate (1.4 mL; 14.7 mmol) was added dropwise and left stirring for 48 h. The mixture was poured into aqueous NaHCO3, extracted with EtOAc (3×25 mL) and the combined organic extracts were washed with brine. The solution was dried over Na2SO4 and the solvent removed. Chromatography on silica gel (eluted with 5% EtOAc in hexane) yielded 1.13g (43%) of the title compound.

Workup

  1. waitleft
  2. stirringstirring for 48 h
  3. extractionextracted with EtOAc (3×25 mL)
  4. washthe combined organic extracts were washed with brine
  5. dry with materialThe solution was dried over Na2SO4
  6. customthe solvent removed

Sources & evidence

ORD record
ord-4be952f4d8694b93983c65c8d7547798
Source dataset
uspto-grants-1996_07
Patent number
US05532237

Reaction notes

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