HCID 66926134, compound → HCID 66925814, compound

HRID 2170826Notes

Reaction equation

HRID 2170826 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[S:12][C:11]([CH3:13])=[C:10]([CH:14]3[C:18](=[O:19])/[C:17](=[CH:20]/[CH:21]4[CH2:26][CH2:25][O:24][CH2:23][CH2:22]4)/[CH2:16][C:15]3=[O:27])[CH:9]=2)=[CH:4][CH:3]=1>C(O)C.[Pd]>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]2[S:12][C:11]([CH3:13])=[C:10]([CH:14]3[C:18](=[O:19])[CH:17]([CH2:20][CH:21]4[CH2:26][CH2:25][O:24][CH2:23][CH2:22]4)[CH2:16][C:15]3=[O:27])[CH:9]=2)=[CH:6][CH:7]=1

Participants

4

Reactant 1

HCID 66926134HCID 66926134, compound

Product 1

HCID 66925814HCID 66925814, compoundYield 48.5%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

To a solution of 2-[5-(4-Chloro-phenyl)-2-methyl-thiophen-3-yl]-4-[1-(tetrahydro-pyran-4-yl)-meth-(E)-ylidene]-cyclopentane-1,3-dione (88 mg, 0.22 mmol) in ethanol (2 ml) was added 5% palladium on carbon (9 mg) and the reaction stirred under an atmosphere of hydrogen at a pressure of 2 bar for 4 hours. The crude reaction mixture was filtered through a pad of Celite and purified by preparative mass-directed HPLC to give 2-[5-(4-Chloro-phenyl)-2-methyl-thiophen-3-yl]-4-(tetrahydro-pyran-4-ylmethyl)-cyclopentane-1,3-dione (43 mg).

Workup

  1. customThe crude reaction mixture
  2. filtrationwas filtered through a pad of Celite
  3. custompurified by preparative mass-directed HPLC

Sources & evidence

ORD record
ord-5ffc58fc27954de092930b8b3d950120
Source dataset
uspto-grants-2015_06
Patent number
US09051300B2

Reaction notes

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