Potassium Carbonate → HCID 66850507, compound

HRID 1948788Notes

Reaction equation

HRID 1948788 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([CH:7]=[CH:8][CH:9]=1)[CH2:5]Br.[CH3:10][Si:11]([CH3:27])([CH3:26])[C:12]1[CH:13]=[CH:14][CH:15]=[C:16]2[C:20]=1[NH:19][C:18]([C:21]([O:23][CH2:24][CH3:25])=[O:22])=[CH:17]2.C(=O)([O-])[O-].[K+].[K+]>C(#N)C>[CH3:10][Si:11]([CH3:26])([CH3:27])[C:12]1[CH:13]=[CH:14][CH:15]=[C:16]2[C:20]=1[N:19]([CH2:5][C:4]1[CH:7]=[CH:8][CH:9]=[C:2]([F:1])[CH:3]=1)[C:18]([C:21]([O:23][CH2:24][CH3:25])=[O:22])=[CH:17]2

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 680073-Fluorobenzyl bromideHCID 66850678HCID 66850678, compound

Product 1

HCID 66850507HCID 66850507, compoundYield 63.2%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

0.42 ml (3.44 mmol) of 3-fluorobenzyl bromide is added, slowly at ambient temperature, to a suspension of 0.75 g (2.87 mmol) of ethyl 7-trimethylsilyl-1H-indole-2-carboxylate, obtained according to the protocol described in stage 5.1, and of 1.18 g (8.61 mmol) of potassium carbonate in 50 ml of dry acetonitrile, maintained under an inert atmosphere. The reaction mixture is stirred at reflux for 18 h. After this period of time, the cooled suspension is filtered through a frit and then rinsed with acetonitrile. The reaction crude obtained after evaporation of the filtrate under reduced pressure is purified by flash chromatography on a silica gel column, elution being carried out with a gradient of 10 to 50% of dichloromethane in heptane. 0.67 g of the expected ethyl 7-trimethylsilyl-1-[(3-fluorophenyl)methyl]-1H-indole-2-carboxylate is thus isolated.

Workup

  1. customobtained
  2. temperatureat reflux for 18 h
  3. waitAfter this period of time
  4. filtrationthe cooled suspension is filtered through a frit
  5. washrinsed with acetonitrile
  6. customThe reaction crude
  7. customobtained
  8. customafter evaporation of the filtrate under reduced pressure
  9. customis purified by flash chromatography on a silica gel column, elution

Sources & evidence

ORD record
ord-5d4a0081b92f4658a0bb123274cf8800
Source dataset
uspto-grants-2013_03
Patent number
US08399491B2

Reaction notes

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