Phthalimide → 2-(1-(2-(3-fluorophenyl)-1,5-naphthyridin-3-yl)ethyl)-1H-isoindole-1,3(2H)-dione

HRID 473400노트

반응식

HRID 473400 반응식
[F:1][C:2]1[CH:3]=[C:4]([C:8]2[C:17]([CH:18](O)[CH3:19])=[CH:16][C:15]3[C:10](=[CH:11][CH:12]=[CH:13][N:14]=3)[N:9]=2)[CH:5]=[CH:6][CH:7]=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[C:40]1(=[O:50])[NH:44][C:43](=[O:45])[C:42]2=[CH:46][CH:47]=[CH:48][CH:49]=[C:41]12.O1CCCC1.N(C(OC(C)C)=O)=NC(OC(C)C)=O>>[F:1][C:2]1[CH:3]=[C:4]([C:8]2[C:17]([CH:18]([N:44]3[C:40](=[O:50])[C:41]4[C:42](=[CH:46][CH:47]=[CH:48][CH:49]=4)[C:43]3=[O:45])[CH3:19])=[CH:16][C:15]3[C:10](=[CH:11][CH:12]=[CH:13][N:14]=3)[N:9]=2)[CH:5]=[CH:6][CH:7]=1

참가 물질

6

반응물 5

HCID 6809PhthalimideHCID 8028TetrahydrofuranHCID 11776TriphenylphosphineHCID 75555Diisopropyl diazene-1,2-dicarboxylateHCID 583186421-(2-(3-Fluorophenyl)-1,5-naphthyridin-3-yl)ethanol

생성물 1

HCID 583186412-(1-(2-(3-fluorophenyl)-1,5-naphthyridin-3-yl)ethyl)-1H-isoindole-1,3(2H)-dione

반응 조건

온도
0 °C

실험 절차

A solution of 1-(2-(3-fluorophenyl)-1,5-naphthyridin-3-yl)ethanol (0.0260 g, 0.0969 mmol), triphenylphosphine (0.0508 g, 0.194 mmol), phthalimide (0.0285 g, 0.194 mmol), and tetrahydrofuran (1.29 mL, 0.0969 mmol) was stirred at room temperature for 5 min to dissolve all reactants. The mixture was then cooled to 0° C. and to the cooled homogenous mixture was added dropwise diisopropyl azodicarboxylate (0.0382 mL, 0.194 mmol) at 0° C. The reaction mixture was allowed to warm to room temperature and stirred at room temperature for 1.5 h. After 1.5 h, the mixture was concentrated under reduced pressure and partitioned between EtOAc (50 mL) and brine (50 mL). The organic layer was dried over Na2SO4, filtered, and concentrated under reduced pressure. The residue was purified by silica gel column chromatography on a 12 g of Redi-Sep™ column using 0 to 100% gradient of EtOAc in hexane over 11 min and 100% isocratic of EtOAc for 25 min as eluent to give 2-(1-(2-(3-fluorophenyl)-1,5-naphthyridin-3-yl)ethyl)-1H-isoindole-1,3(2H)-dione as a white solid: LC-MS (ESI) m/z 397.9 [M+H]+.

후처리

  1. dissolutionto dissolve all reactants
  2. temperatureto warm to room temperature
  3. waitAfter 1.5 h
  4. concentrationthe mixture was concentrated under reduced pressure
  5. custompartitioned between EtOAc (50 mL) and brine (50 mL)
  6. dry with materialThe organic layer was dried over Na2SO4
  7. filtrationfiltered
  8. concentrationconcentrated under reduced pressure
  9. customThe residue was purified by silica gel column chromatography on a 12 g of Redi-Sep™ column
  10. customover 11 min

출처 및 근거

ORD 기록
ord-11ce75a0f85a411bb6e5ad086381cce2
출처 데이터셋
uspto-grants-2014_01
특허 번호
US08633313B2

반응 노트

불러오는 중…