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

HRID 1445499Notes

Reaction equation

HRID 1445499 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-124081047e784fcfbc2ca9b155d5d5f7
Source dataset
uspto-grants-2010_02
Patent number
US07666868B2

Reaction notes

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