HCID 66926091, compound → HCID 66926106, compound

HRID 2170796Notes

Reaction equation

HRID 2170796 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:12]=[C:11]([CH3:13])[N:10]([CH:14]3[C:18](=[O:19])/[C:17](=[CH:20]\[C:21]4[CH:26]=[CH:25][C:24]([F:27])=[CH:23][N:22]=4)/[CH2:16][C:15]3=[O:28])[N:9]=2)=[CH:4][CH:3]=1.[H][H]>CO.[Pd]>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:12]=[C:11]([CH3:13])[N:10]([CH:14]3[C:18](=[O:19])[CH:17]([CH2:20][C:21]4[CH:26]=[CH:25][C:24]([F:27])=[CH:23][N:22]=4)[CH2:16][C:15]3=[O:28])[N:9]=2)=[CH:4][CH:3]=1

Participants

5

Reactant 2

HCID 66926091HCID 66926091, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 66926106HCID 66926106, compoundYield 98.7%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

To a solution of 2-[3-(4-chloro-phenyl)-5-methyl-pyrazol-1-yl]-4-[1-(5-fluoro-pyridin-2-yl)-meth-(Z)-ylidene]-cyclopentane-1,3-dione (17 mg, 0.04 mmol) in methanol (0.4 ml) was added 5% palladium on activated charcoal (2 mg) and the reaction stirred for 6 hours under 1.5 bar of hydrogen. The solution was then filtered through a pad of Celite, washed with methanol (10 ml) and concentrated in vacuo to give a white solid, which was purified by column chromatography using DCM:EtOAc:AcOH (9:1:0.01%) to (3:7:0.01%) to give 2-[3-(4-chloro-phenyl)-5-methyl-pyrazol-1-yl]-4-(5-fluoro-pyridin-2-ylmethyl)-cyclopentane-1,3-dione (15.7 mg).

Workup

  1. filtrationThe solution was then filtered through a pad of Celite
  2. washwashed with methanol (10 ml)
  3. concentrationconcentrated in vacuo
  4. customto give a white solid, which
  5. customwas purified by column chromatography

Sources & evidence

ORD record
ord-de6b76ea9d7d43d7b0bba166a70712c3
Source dataset
uspto-grants-2015_06
Patent number
US09051300B2

Reaction notes

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