Ethyl bromoacetate → [5-(Tert-butyl-dimethyl-silanyloxy)-indol-1-yl]-acetic acid ethyl ester

HRID 890418Notes

Reaction equation

HRID 890418 reaction equation
[C:1]([Si:5]([CH3:17])([CH3:16])[O:6][C:7]1[CH:8]=[C:9]2[C:13](=[CH:14][CH:15]=1)[NH:12][CH:11]=[CH:10]2)([CH3:4])([CH3:3])[CH3:2].Br[CH2:19][C:20]([O:22][CH2:23][CH3:24])=[O:21].C(=O)([O-])[O-].[Cs+].[Cs+]>CN(C=O)C.CCOCC>[CH2:23]([O:22][C:20](=[O:21])[CH2:19][N:12]1[C:13]2[C:9](=[CH:8][C:7]([O:6][Si:5]([C:1]([CH3:4])([CH3:3])[CH3:2])([CH3:17])[CH3:16])=[CH:15][CH:14]=2)[CH:10]=[CH:11]1)[CH3:24]

Participants

6

Reactant 3

HCID 7748Ethyl bromoacetateHCID 10796Cesium carbonateHCID 222508175-(tert-Butyldimethylsilyloxy)-1H-indole

Product 1

HCID 68822475[5-(Tert-butyl-dimethyl-silanyloxy)-indol-1-yl]-acetic acid ethyl ester

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 6228DimethylformamideSolvent

Procedure

To a solution of 9.2 g (37.18 mmol) 5-(tert-butyl-dimethyl-silanyloxy)-1H-indole and 4.79 ml (40.9 mmol) ethyl bromoacetate in 140 ml of DMF was added 36.35 g (111.5 mmol) of cesium carbonate. The reaction mixture was stirred for 3 h at RT, taken up in ether and then washed with 1N HCl and water. The ether phase was concentrated under reduced pressure to give 12.93 g (quant.) of almost pure [5-(tert-butyl-dimethyl-silanyloxy)-indol-1-yl]-acetic acid ethyl ester.

Workup

  1. washwashed with 1N HCl and water
  2. concentrationThe ether phase was concentrated under reduced pressure

Sources & evidence

ORD record
ord-417c1585eee143daaf533eb7fb894869
Source dataset
uspto-grants-2006_02
Patent number
US06995263B2

Reaction notes

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