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

HRID 1496862Notes

Reaction equation

[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

Participants

Conditions

Temperature: 70 °C

Procedure

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.

Workup

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

Sources & evidence

ORD record: ord-274b31d320a940698bd30dab35cca1d7
Source dataset: uspto-grants-2015_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09199937B2

Reaction notes

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