Tetrahydrofuran → 1H-Indole-7-carboxaldehyde, 6-fluoro-2,3-dihydro-

HRID 557224노트

반응식

HRID 557224 반응식
C([Li])(C)(C)C.C(OC([N:13]1[C:21]2[C:16](=[CH:17][CH:18]=[C:19]([F:22])[CH:20]=2)[CH2:15][CH2:14]1)=O)(C)(C)C.[O:23]1CCC[CH2:24]1>>[F:22][C:19]1[C:20]([CH:24]=[O:23])=[C:21]2[C:16]([CH2:15][CH2:14][NH:13]2)=[CH:17][CH:18]=1

참가 물질

4

반응물 3

HCID 8028TetrahydrofuranHCID 17985580Tert-butyl 6-fluoroindoline-1-carboxylateHCID 178418306HCID 178418306, 화합물

생성물 1

HCID 179858381H-Indole-7-carboxaldehyde, 6-fluoro-2,3-dihydro-수율 42%

실험 절차

Add tert-butyllithium (21.13 ml, 35.93 mmol, 1.7 M solution in heptane) to a solution of 1-(tert-butoxycarbonyl)-2,3-dihydro-6-fluoroindole (3.28 g, 13.82 mmol) in anhydrous tetrahydrofuran (100 ml) at −78 C. Stir for 20 minutes, quench with excess dimethylformamide, and stir for 1 hour at −78 C. Warm to room temperature, add saturated aqueous ammonium chloride, and extract with ethyl acetate. Concentrate the combined organic phases under reduced pressure and subject the residue to silica gel chromatography to provide the desired compound as a bright yellow solid (0.91 g, 42%).

후처리

  1. customquench with excess dimethylformamide
  2. stirringstir for 1 hour at −78 C
  3. additionadd saturated aqueous ammonium chloride
  4. extractionextract with ethyl acetate
  5. concentrationConcentrate the combined organic phases under reduced pressure

출처 및 근거

ORD 기록
ord-d6497d076ccd403bba13a0007ac9ae9f
출처 데이터셋
uspto-grants-2011_11
특허 번호
US08058425B2

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