3-(1-(Tert-butyldimethylsilyloxy)vinyl)-2-(pyridin-2-ylethynyl)pyridine → 7-(Pyridin-2-yl)quinolin-5-ol

HRID 1496862노트

반응식

HRID 1496862 반응식
[Si]([O:8][C:9]([C:11]1[C:12]([C:17]#[C:18][C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][N:20]=2)=[N:13][CH:14]=[CH:15][CH:16]=1)=[CH2:10])(C(C)(C)C)(C)C>C(COC)OC.C(Cl)Cl.[Ag+].FC(F)(F)S([O-])(=O)=O>[N:20]1[CH:21]=[CH:22][CH:23]=[CH:24][C:19]=1[C:18]1[CH:10]=[C:9]([OH:8])[C:11]2[CH:16]=[CH:15][CH:14]=[N:13][C:12]=2[CH:17]=1

참가 물질

5

반응물 1

HCID 866761033-(1-(Tert-butyldimethylsilyloxy)vinyl)-2-(pyridin-2-ylethynyl)pyridine

생성물 1

HCID 1364132527-(Pyridin-2-yl)quinolin-5-ol수율 24.4%

시약·촉매·용매 3

HCID 76223Silver(I) trifluoromethanesulfonate촉매HCID 6344Dichloromethane용매HCID 80711,2-Dimethoxyethane용매

반응 조건

온도
70 °C

실험 절차

Step 3 (=Reaction 5): 1.025 g 3-(1-(tert-butyldimethylsilyloxy)vinyl)-2-(pyridin-2-ylethynyl)pyridine was dissolved in 100 mL dimethoxyethane and 126 mg of trifluormethanesulfonic acid silver salt added and stirred 7 h at 70° C. The mixture is diluted with DCM and extracted with saturated NaHCO3 solution (3×). The organic phase was dried (MgSO4) and concentrated in vaccuo. The residual mixture was dissolved in 10 mL THF, 1.2 mL of tertbutylammoniumfluoride in THF (1N) was added and the mixture stirred for 2 h at 25° C. The mixture was diluted with DCM and extracted with water (1×) and the organic phase concentrated in vacuo and purified via FCC (100 g SiO2, DCM→DCM 93:7) to yield 165 mg of 7-(pyridin-2-yl)quinolin-5-ol 6.3 as solid. HPLC-MS: Rt=0.78 min (method E), M+H=223.

후처리

  1. customStep 3 (=Reaction 5)
  2. extractionextracted with saturated NaHCO3 solution (3×)
  3. dry with materialThe organic phase was dried (MgSO4)
  4. concentrationconcentrated in vaccuo
  5. dissolutionThe residual mixture was dissolved in 10 mL THF
  6. addition1.2 mL of tertbutylammoniumfluoride in THF (1N) was added
  7. stirringthe mixture stirred for 2 h at 25° C
  8. additionThe mixture was diluted with DCM
  9. extractionextracted with water (1×)
  10. concentrationthe organic phase concentrated in vacuo
  11. custompurified via FCC (100 g SiO2, DCM→DCM 93:7)

출처 및 근거

ORD 기록
ord-274b31d320a940698bd30dab35cca1d7
출처 데이터셋
uspto-grants-2015_12
특허 번호
US09199937B2

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