Potassium Carbonate → HCID 43152087, compound

HRID 571207Notes

Reaction equation

HRID 571207 reaction equation
[N+:1]([C:4]1[CH:5]=[C:6]2[C:10](=[CH:11][CH:12]=1)[NH:9][CH:8]=[CH:7]2)([O-:3])=[O:2].C([O-])([O-])=O.[K+].[K+].Br[CH2:20][C:21]([O:23][CH3:24])=[O:22]>CN(C=O)C>[N+:1]([C:4]1[CH:5]=[C:6]2[C:10](=[CH:11][CH:12]=1)[N:9]([CH2:20][C:21]([O:23][CH3:24])=[O:22])[CH:8]=[CH:7]2)([O-:3])=[O:2]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 225235-NitroindoleHCID 60984Methyl bromoacetate

Product 1

HCID 43152087HCID 43152087, compoundYield 58%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 5-nitro-1H-indole (1 g, 6.17 mmol) in DMF (15 ml), K2CO3 (1.023 g, 7.40 mmol) and methyl 2-bromoacetate (0.686 ml, 7.40 mmol) were added, and the mixture was reacted under MW irradiation for 1 hour at 100° C. The insoluble inorganic salts were filtered off, the solvent was removed and the resulting crude was purified by flash chromatography on silica gel column (petroleum ether:ethyl acetate=8:2) to afford methyl 2-(5-nitro-1H-indol-1-yl)acetate (830 mg, 3.54 mmol, 58% yield). MS/ESI+ 234.2[MH]+.

Workup

  1. customthe mixture was reacted under MW irradiation for 1 hour at 100° C
  2. filtrationThe insoluble inorganic salts were filtered off
  3. customthe solvent was removed
  4. customthe resulting crude was purified by flash chromatography on silica gel column (petroleum ether:ethyl acetate=8:2)

Sources & evidence

ORD record
ord-cc3be984bf6f49a888dbc9e950208e6f
Source dataset
uspto-grants-2015_05
Patent number
US09024027B2

Reaction notes

Loading…