Potassium Carbonate → 1-(4,7-dimethoxy-1H-pyrrolo[2,3-c]pyridin-3-yl)-2-[4-(1-phenylprop-2-ynylidene)-1-piperidyl]ethane-1,2-dione

HRID 606752Notes

Reaction equation

HRID 606752 reaction equation
[C:1]1([C:7](=[C:14]2[CH2:19][CH2:18][N:17]([C:20](=[O:36])[C:21]([C:23]3[C:31]4[C:26](=[C:27]([O:34][CH3:35])[N:28]=[CH:29][C:30]=4[O:32][CH3:33])[NH:25][CH:24]=3)=[O:22])[CH2:16][CH2:15]2)[C:8]#[C:9][Si](C)(C)C)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C([O-])([O-])=O.[K+].[K+]>CO>[C:1]1([C:7](=[C:14]2[CH2:15][CH2:16][N:17]([C:20](=[O:36])[C:21]([C:23]3[C:31]4[C:26](=[C:27]([O:34][CH3:35])[N:28]=[CH:29][C:30]=4[O:32][CH3:33])[NH:25][CH:24]=3)=[O:22])[CH2:18][CH2:19]2)[C:8]#[CH:9])[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

4

Reactant 2

HCID 11430Potassium CarbonateHCID 52799201-(4,7-dimethoxy-1H-pyrrolo[2,3-c]pyridin-3-yl)-2-[4-(1-phenyl-3-trimethylsilyl-prop-2-ynylidene)-1-piperidyl]ethane-1,2-dione

Product 1

HCID 52799211-(4,7-dimethoxy-1H-pyrrolo[2,3-c]pyridin-3-yl)-2-[4-(1-phenylprop-2-ynylidene)-1-piperidyl]ethane-1,2-dioneYield 91%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of 1-[4-(1-phenyl-1-(2-trimethylsilylethyn-1-yl)-methylene)-piperidin-1-yl]-2-(4,7-dimethoxy-6-azaindol-3-yl)-ethane-1,2-dione (0.035 g, 0.0699 mmol) in MeOH (1 mL) was added K2CO3 (0.010 g, 0.0724 mmol) and the mixture was allowed to stir at room temperature for 6 h. The mixture was then evaporated and the residue was purified by preparative HPLC to give the title compound as a colorless solid (0.027. g, 91%).

Workup

  1. customThe mixture was then evaporated
  2. customthe residue was purified by preparative HPLC

Sources & evidence

ORD record
ord-3a9ffc95d7e6479ea58557c4b91fef05
Source dataset
uspto-grants-2011_03
Patent number
US07915283B2

Reaction notes

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