Potassium Carbonate → HCID 59145843, compound

HRID 887796

Reaction equation

HRID 887796 reaction equation
[NH2:1]OS(C1C(C)=CC(C)=CC=1C)(=O)=O.[CH:15]1[C:20]2[CH:21]([CH2:24][C:25]#[N:26])[CH2:22][CH2:23][C:19]=2[CH:18]=[CH:17][N:16]=1.[C:27]1([C:33]#[C:34][C:35]([O:37][CH3:38])=[O:36])[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1.C(=O)([O-])[O-].[K+].[K+]>C(#N)C.O.CN(C)C=O>[C:25]([CH2:24][CH:21]1[C:20]2[C:15]3[N:16]([N:1]=[C:33]([C:27]4[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=4)[C:34]=3[C:35]([O:37][CH3:38])=[O:36])[CH:17]=[CH:18][C:19]=2[CH2:23][CH2:22]1)#[N:26]

Participants

8

Reactant 4

HCID 11430Potassium CarbonateHCID 138378Phenylpropynoic acid methyl esterHCID 11830845O-(2,4,6-Trimethylbenzenesulfonyl)hydroxylamineHCID 59145894HCID 59145894, compound

Product 1

HCID 59145843HCID 59145843, compoundYield 34.7%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6228DimethylformamideSolventHCID 6342AcetonitrileSolvent2×

Procedure

To a solution of 2-[(aminooxy)sulfonyl]-1,3,5-trimethylbenzene (about 16.4 mmol) in acetonitrile (80 mL) was added a solution of 6,7-dihydro-5H-cyclopenta[c]pyridin-7-ylacetonitrile (1.30 g, 8.22 mmol) in acetonitrile (40 mL), and the mixture was stirred at room temperature for 30 min. N,N-Dimethylformamide (40 mL) was added, and the mixture was concentrated under reduced pressure. To 46% of the residual solution were added methyl 3-phenylpropiolate (671 μL, 4.55 mmol) and potassium carbonate (1.31 g, 9.48 mmol), and the mixture was stirred at room temperature for 18 hr. The reaction solution was diluted with water, and the mixture was extracted with ethyl acetate. The extract was washed with saturated brine, and dried over anhydrous sodium sulfate. The solvent was evaporated under reduced pressure, and the residue was purified by silica gel column chromatography (ethyl acetate/hexane=25/75) to give the title compound (523 mg).

Workup

  1. concentrationthe mixture was concentrated under reduced pressure
  2. stirringthe mixture was stirred at room temperature for 18 hr
  3. extractionthe mixture was extracted with ethyl acetate
  4. washThe extract was washed with saturated brine
  5. dry with materialdried over anhydrous sodium sulfate
  6. customThe solvent was evaporated under reduced pressure
  7. customthe residue was purified by silica gel column chromatography (ethyl acetate/hexane=25/75)

Sources & evidence

ORD record
ord-61ee8133a87844289076b402c807ff18
Source dataset
uspto-grants-2012_08
Patent number
US08247429B2

Linked notes

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