Potassium Fluoride → (E)-3-[1-(4-Ethynyl-benzenesulfonyl)-1H-pyrrol-3-yl]-N-(tetrahydro-pyran-2-yloxy)-acrylamide

HRID 2408451Notes

Reaction equation

HRID 2408451 reaction equation
[O:1]1[CH2:6][CH2:5][CH2:4][CH2:3][CH:2]1[O:7][NH:8][C:9](=[O:32])/[CH:10]=[CH:11]/[C:12]1[CH:16]=[CH:15][N:14]([S:17]([C:20]2[CH:25]=[CH:24][C:23]([C:26]#[C:27][Si](C)(C)C)=[CH:22][CH:21]=2)(=[O:19])=[O:18])[CH:13]=1.[F-].[K+]>CO>[C:26]([C:23]1[CH:24]=[CH:25][C:20]([S:17]([N:14]2[CH:15]=[CH:16][C:12](/[CH:11]=[CH:10]/[C:9]([NH:8][O:7][CH:2]3[CH2:3][CH2:4][CH2:5][CH2:6][O:1]3)=[O:32])=[CH:13]2)(=[O:19])=[O:18])=[CH:21][CH:22]=1)#[CH:27]

Participants

4

Reactant 2

HCID 522689Potassium FluorideHCID 86621703(E)-N-(Tetrahydro-pyran-2-yloxy)-3-[1-(4-trimethylsilanylethynyl-benzenesulfonyl)-1H-pyrrol-3-yl]-acrylamide

Product 1

HCID 86621705(E)-3-[1-(4-Ethynyl-benzenesulfonyl)-1H-pyrrol-3-yl]-N-(tetrahydro-pyran-2-yloxy)-acrylamide

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a stirred solution of (E)-N-(Tetrahydro-pyran-2-yloxy)-3-[1-(4-trimethylsilanylethynyl-benzenesulfonyl)-1H-pyrrol-3-yl]-acrylamide (0.139 mmol) in methanol (1.2 ml) is added KF (0.26 mmol). After 15 min the solvent is evaporated and the residue is taken up in DCM and filtered over alumina (1 g, neutral, activity II-III) using DCM as eluent. After evaporation of the solvent 0.0801 mmol of the title compound are obtained.

Workup

  1. customAfter 15 min the solvent is evaporated
  2. filtrationfiltered over alumina (1 g, neutral, activity II-III)

Sources & evidence

ORD record
ord-b630085a956f4b0eba69560eaec2457f
Source dataset
uspto-grants-2014_08
Patent number
US08815855B2

Reaction notes

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