Chlorotrimethylsilane → 1-ethyl-4-fluoro-2-naphthalen-1-yl-5-trimethylsilanyl-1H-imidazole

HRID 12466

반응식

HRID 12466 반응식
Br[C:2]1[N:3]=[C:4]([C:10]2[C:19]3[C:14](=[CH:15][CH:16]=[CH:17][CH:18]=3)[CH:13]=[CH:12][CH:11]=2)[N:5]([CH2:8][CH3:9])[C:6]=1Br.[Li]CCCC.CCCCCC.[CH3:31][Si:32](Cl)([CH3:34])[CH3:33].C1C=CC(S(N(S(C2C=CC=CC=2)(=O)=O)[F:46])(=O)=O)=CC=1>C1COCC1.O>[CH2:8]([N:5]1[C:6]([Si:32]([CH3:34])([CH3:33])[CH3:31])=[C:2]([F:46])[N:3]=[C:4]1[C:10]1[C:19]2[C:14](=[CH:15][CH:16]=[CH:17][CH:18]=2)[CH:13]=[CH:12][CH:11]=1)[CH3:9]

참가 물질

8

반응물 5

HCID 6397ChlorotrimethylsilaneHCID 8058Hexane2회HCID 588007N-FluorobenzenesulfonimideHCID 534259994,5-Dibromo-1-ethyl-2-(naphthalen-1-yl)-1H-imidazoleHCID 178418339Butyllithium2회

생성물 1

HCID 686294501-ethyl-4-fluoro-2-naphthalen-1-yl-5-trimethylsilanyl-1H-imidazole

시약·촉매·용매 2

HCID 962Water용매HCID 8028Tetrahydrofuran용매

반응 조건

온도
-78 °C

실험 절차

To a solution of 4,5-dibromo-1-ethyl-2-naphthalen-1-yl-1H-imidazole (6.55 g, 17.2 mmol) in anhydrous THF (150 ml) at −78° C. under nitrogen is added a solution of n-BuLi in hexane (1.6 M, 11.8 ml, 19 mmol, 1.1 eq.) dropwise. The resulting mixture is stirred at −78° C. for 1 hr, and TMSCl (2.05 g, 19 mmol, 1.1 eq.) is added. The resulting solution is stirred at −78° C. After 1 hr, n-BuLi in hexane (1.6 M, 11.8 ml, 19 mmol, 1.1 eq.) is added dropwise. The resulting mixture is stirred at −78° C. for 1 hr, and N-fluorobenzenesulfonimide (5.99 g, 19 mmol, 1.1 eq.) is added. The resulting solution is stirred at −78° C. for 2 hr, warmed to rt slowly, and then stirred at rt overnight. Water (50 ml) is added to quench the reaction, and THF is evaporated. The residue is extracted with EtOAc (75 ml×2) and the combined organic layers are washed with water and brine, dried and concentrated to give crude 1-ethyl-4-fluoro-2-naphthalen-1-yl-5-trimethylsilanyl-1H-imidazole as a yellow oil. LCMS 313 (M+1).

후처리

  1. stirringThe resulting solution is stirred at −78° C
  2. waitAfter 1 hr
  3. stirringThe resulting mixture is stirred at −78° C. for 1 hr
  4. stirringThe resulting solution is stirred at −78° C. for 2 hr
  5. temperaturewarmed to rt slowly
  6. stirringstirred at rt overnight
  7. customto quench
  8. customthe reaction, and THF
  9. customis evaporated
  10. extractionThe residue is extracted with EtOAc (75 ml×2)
  11. washthe combined organic layers are washed with water and brine
  12. customdried
  13. concentrationconcentrated

출처 및 근거

ORD 기록
ord-063302fd527f4632a4a26455de7386ac
출처 데이터셋
uspto-grants-2010_06
특허 번호
US07728009B1

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