Ethyl bromoacetate → HCID 20087973, compound

HRID 275362Notes

Reaction equation

HRID 275362 reaction equation
Br[CH2:2][C:3]([O:5][CH2:6]C)=[O:4].[F:8][C:9]1[CH:14]=[CH:13][C:12]([C:15]2[C:23]3[C:18](=[CH:19][CH:20]=[C:21]([CH3:24])[CH:22]=3)[N:17]([CH:25]3[CH2:30][CH2:29][NH:28][CH2:27][CH2:26]3)[CH:16]=2)=[CH:11][CH:10]=1.C([O-])([O-])=O.[K+].[K+]>CC(C)=O>[F:8][C:9]1[CH:14]=[CH:13][C:12]([C:15]2[C:23]3[C:18](=[CH:19][CH:20]=[C:21]([CH3:24])[CH:22]=3)[N:17]([CH:25]3[CH2:30][CH2:29][N:28]([CH2:2][C:3]([O:5][CH3:6])=[O:4])[CH2:27][CH2:26]3)[CH:16]=2)=[CH:11][CH:10]=1

Participants

5

Reactant 3

HCID 7748Ethyl bromoacetateHCID 11430Potassium CarbonateHCID 10063879HCID 10063879, compound

Product 1

HCID 20087973HCID 20087973, compound

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent2×

Procedure

A solution of ethyl bromoacetate in acetone was added during 15 min to a mixture of 3-(4-fluorophenyl)-5-methyl-l-(4-piperidyl)-1H-indole 3d (5.0 g), K2CO3 (2.5 g) and acetone (100 ml) at room temperature. After another 2 h the solvents were evaporated, water was added and the mixture was extracted with ethyl acetate (2×100 ml). The combined organic phases were washed with brine and dried (Na2SO4). Evaporation of the solvent afforded the crude methyl 4-[3-(4-fluorophenyl)-5-methyl-1H-indol-1-yl]1-piperidinacetate (6.0 g), which was used without further purification.

Workup

  1. customAfter another 2 h the solvents were evaporated
  2. additionwater was added
  3. extractionthe mixture was extracted with ethyl acetate (2×100 ml)
  4. washThe combined organic phases were washed with brine
  5. dry with materialdried (Na2SO4)
  6. customEvaporation of the solvent

Sources & evidence

ORD record
ord-f405fe3cc3594b4ab961c543ad485080
Source dataset
uspto-grants-1995_02
Patent number
US05393761

Reaction notes

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