Potassium Carbonate → HCID 19085273, compound

HRID 963093Notes

Reaction equation

HRID 963093 reaction equation
[F:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[NH:7][C:6]([C:11]([O:13][CH2:14][C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1)=[O:12])=[CH:5]2.C(=O)([O-])[O-].[K+].[K+].[C:27]([O:30][CH2:31][CH2:32]Br)(=[O:29])[CH3:28]>CN(C=O)C>[CH2:31]([O:30][C:27]([CH2:28][N:7]1[C:8]2[C:4](=[CH:3][C:2]([F:1])=[CH:10][CH:9]=2)[CH:5]=[C:6]1[C:11]([O:13][CH2:14][C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1)=[O:12])=[O:29])[CH3:32]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 135641-Acetoxy-2-bromoethaneHCID 190853401H-Indole-2-carboxylic acid, 5-fluoro-, phenylmethyl ester

Product 1

HCID 19085273HCID 19085273, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Benzyl 5-fluoroindole-2-carboxylate (9.4 g) was dissolved in DMF (94 ml). Potassium carbonate (9.7 g) and bromoethyl acetate (4.0 ml) were added and the mixture was stirred for 5 hours. The reaction mixture was partitioned between ethyl acetate and water. The organic layer was washed with saturated brine and dried over magnesium sulfate. The solvent was evaporated, and the residue was recrystallized from isopropyl alcohol to give 9.59 g of benzyl 1-ethoxycarbonylmethyl-5-fluoroindole-2-carboxylate.

Workup

  1. customThe reaction mixture was partitioned between ethyl acetate and water
  2. washThe organic layer was washed with saturated brine
  3. dry with materialdried over magnesium sulfate
  4. customThe solvent was evaporated
  5. customthe residue was recrystallized from isopropyl alcohol

Sources & evidence

ORD record
ord-02ed9b25a94f4d80844ed4562d6bc8ed
Source dataset
uspto-grants-1998_06
Patent number
US05760032

Reaction notes

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