Potassium Carbonate → ethyl 5-trimethylsilyl-1-[(3-fluorophenyl)methyl]-1H-indole-2-carboxylate

HRID 1948786Notes

Reaction equation

HRID 1948786 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]=[C:14]2[C:18](=[CH:19][CH:20]=1)[NH:17][C:16]([C:21]([O:23][CH2:24][CH3:25])=[O:22])=[CH:15]2.C(=O)([O-])[O-].[K+].[K+]>[Br-].C([N+](CCCC)(CCCC)CCCC)CCC.C(#N)C>[CH3:10][Si:11]([CH3:26])([CH3:27])[C:12]1[CH:13]=[C:14]2[C:18](=[CH:19][CH:20]=1)[N:17]([CH2:5][C:4]1[CH:7]=[CH:8][CH:9]=[C:2]([F:1])[CH:3]=1)[C:16]([C:21]([O:23][CH2:24][CH3:25])=[O:22])=[CH:15]2

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 680073-Fluorobenzyl bromideHCID 66845842ethyl 5-trimethylsilyl-1H-indole-2-carboxylate

Product 1

HCID 66850361ethyl 5-trimethylsilyl-1-[(3-fluorophenyl)methyl]-1H-indole-2-carboxylateYield 88.4%

Reagents, catalysts & solvents 2

HCID 74236Tetrabutylammonium BromideCatalystHCID 6342AcetonitrileSolvent

Procedure

0.32 g (1.68 mmol) of 3-fluorobenzyl bromide and 100 mg (0.31 mmol) of tetrabutyl-ammonium bromide are added, slowly at ambient temperature, to a suspension of 0.4 g (1.53 mmol) of ethyl 5-trimethylsilyl-1H-indole-2-carboxylate, obtained according to the protocol described in stage 3.4, and of 0.64 g (4.59 mmol) of potassium carbonate in 15 ml of dry acetonitrile, maintained under an inert atmosphere. The reaction mixture is stirred at reflux for 2 h. After this period of time, the cooled suspension is filtered through a frit and 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 5 to 15% of ether in heptane. 0.5 g of the expected ethyl 5-trimethylsilyl-1-[(3-fluorophenyl)methyl]-1H-indole-2-carboxylate is thus isolated.

Workup

  1. customobtained
  2. temperatureat reflux for 2 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-5fc181b042854e8b859a8a13a975fcf6
Source dataset
uspto-grants-2013_03
Patent number
US08399491B2

Reaction notes

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