Triisopropylsilyl trifluoromethanesulfonate → 4-{2-(4-Fluorophenyl)-1-[tri(propan-2-yl)silyl]-1H-pyrrol-3-yl}pyridine

HRID 1244988Notes

Reaction equation

HRID 1244988 reaction equation
C([Li])CCC.[F:6][C:7]1[CH:12]=[CH:11][C:10]([C:13]2[NH:14][CH:15]=[CH:16][C:17]=2[C:18]2[CH:23]=[CH:22][N:21]=[CH:20][CH:19]=2)=[CH:9][CH:8]=1.O([Si:32]([CH:39]([CH3:41])[CH3:40])([CH:36]([CH3:38])[CH3:37])[CH:33]([CH3:35])[CH3:34])S(C(F)(F)F)(=O)=O>CCCCCC.O1CCCC1>[F:6][C:7]1[CH:8]=[CH:9][C:10]([C:13]2[N:14]([Si:32]([CH:39]([CH3:41])[CH3:40])([CH:36]([CH3:38])[CH3:37])[CH:33]([CH3:35])[CH3:34])[CH:15]=[CH:16][C:17]=2[C:18]2[CH:23]=[CH:22][N:21]=[CH:20][CH:19]=2)=[CH:11][CH:12]=1

Participants

6

Reactant 3

HCID 2724529Triisopropylsilyl trifluoromethanesulfonateHCID 219226632-(4-Fluorophenyl)-3-(pyridin-4-yl)-1H-pyrroleHCID 178418339Butyllithium

Product 1

HCID 219227124-{2-(4-Fluorophenyl)-1-[tri(propan-2-yl)silyl]-1H-pyrrol-3-yl}pyridineYield 100%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8058HexaneSolvent

Procedure

31 ml (47.4 mmol) of a 1.57 N solution of butyllithium in hexane were added to a solution of 11.30 g (47.4 mmol) of 2-(4-fluorophenyl)-3-(pyridin-4-yl)-1H-pyrrole [prepared as described in step 7(i) above] in 300 ml of tetrahydrofuran at −78° C. and the mixture was stirred for 10 minutes. At the end of this time, 13.4 ml (49.8 mmol) of triisopropylsilyl triflate were added to the reaction mixture at the same temperature. After removal of the cooling bath, the mixture was stirred at room temperature for 30 minutes. 200 ml of water and 300 ml of a saturated aqueous solution of sodium hydrogencarbonate were then added to the reaction mixture before extracting with ethyl acetate. The organic extract was washed with water, dried over anhydrous sodium sulfate and then concentrated by evaporation under reduced pressure to give 18.70 g (quantitative yield) of the title compound as a reddish purple oil.

Workup

  1. customAfter removal of the cooling bath
  2. stirringthe mixture was stirred at room temperature for 30 minutes
  3. addition200 ml of water and 300 ml of a saturated aqueous solution of sodium hydrogencarbonate were then added to the reaction mixture
  4. extractionbefore extracting with ethyl acetate
  5. extractionThe organic extract
  6. washwas washed with water
  7. dry with materialdried over anhydrous sodium sulfate
  8. concentrationconcentrated by evaporation under reduced pressure

Sources & evidence

ORD record
ord-7092c604d365482ebce203546e1c81f8
Source dataset
uspto-grants-2006_10
Patent number
US07122666B2

Reaction notes

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