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

HRID 1402709Notes

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

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 vacuo. 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

extractionextracted with saturated NaHCO3 solution (3×)
dry with materialThe organic phase was dried (MgSO4)
concentrationconcentrated in vacuo
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-5edbf4d323a7496ea38ae1f109e42d51
Source dataset: uspto-grants-2014_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08912173B2

Reaction notes

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