Potassium Carbonate → HCID 86681614, compound

HRID 571195

Reaction equation

HRID 571195 reaction equation
[N+:1]([C:4]1[CH:5]=[CH:6][CH:7]=[C:8]2[C:12]=1[NH:11][CH:10]=[CH:9]2)([O-:3])=[O:2].C([O-])([O-])=O.[K+].[K+].Br[CH2:20][C:21]([O:23][CH3:24])=[O:22]>CC#N>[N+:1]([C:4]1[CH:5]=[CH:6][CH:7]=[C:8]2[C:12]=1[N:11]([CH2:20][C:21]([O:23][CH3:24])=[O:22])[CH:10]=[CH:9]2)([O-:3])=[O:2]

Participants

5

Reactant 3

HCID 11430Potassium Carbonate2×HCID 233967-NitroindoleHCID 60984Methyl bromoacetate2×

Product 1

HCID 86681614HCID 86681614, compoundYield 51%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

To a solution of 7-nitro-1H-indole (0.5 g, 3.08 mmol) in dry CH3CN (20 ml), K2CO3 (0.511 g, 3.70 mmol) was added at room temperature. After 10 minutes, methyl 2-bromoacetate (0.343 ml, 3.70 mmol) was added dropwise, and the reaction was refluxed for 24 hours. Additional K2CO3 (0.511 g, 3.70 mmol) and methyl 2-bromoacetate (0.343 ml, 3.70 mmol) were added, and the stirring was prolonged for further 16 hours. The reaction was cooled at room temperature and the solvent was evaporated under vacuum. The resulting crude was partitioned between water and DCM; the organic phase was dried over sodium sulfate and evaporated under vacuum. The crude was purified by flash column chromatography on silica gel (hexane:ethyl acetate=9:1) affording methyl 2-(7-nitro-1H-indol-1-yl)acetate that crystallizes on standing (0.37 g, 1.580 mmol, 51% yield). MS/ESI+ 234.9 [MH]+.

Workup

  1. temperaturethe reaction was refluxed for 24 hours
  2. waitthe stirring was prolonged for further 16 hours
  3. customthe solvent was evaporated under vacuum
  4. customThe resulting crude was partitioned between water and DCM
  5. dry with materialthe organic phase was dried over sodium sulfate
  6. customevaporated under vacuum
  7. customThe crude was purified by flash column chromatography on silica gel (hexane:ethyl acetate=9:1)

Sources & evidence

ORD record
ord-3b88eb2600b1460fb4224f3d9fb5ecd4
Source dataset
uspto-grants-2015_05
Patent number
US09024027B2

Linked notes

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