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

HRID 1244988ノート

反応式

HRID 1244988 の反応式
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

参加物

6

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 2

HCID 8028Tetrahydrofuran溶媒HCID 8058Hexane溶媒

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-7092c604d365482ebce203546e1c81f8
出典データセット
uspto-grants-2006_10
特許番号
US07122666B2

反応ノート

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