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

HRID 1496862ノート

反応式

HRID 1496862 の反応式
[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

参加物

5

反応物 1

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

生成物 1

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

試薬・触媒・溶媒 3

HCID 76223Silver(I) trifluoromethanesulfonate触媒HCID 6344Dichloromethane溶媒HCID 80711,2-Dimethoxyethane溶媒

反応条件

温度
70 °C

実験手順

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.

後処理

  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)

出典と根拠

ORDレコード
ord-274b31d320a940698bd30dab35cca1d7
出典データセット
uspto-grants-2015_12
特許番号
US09199937B2

反応ノート

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