HCID 69064639, compound → HCID 11566962, compound

HRID 1817495Notes

Reaction equation

HRID 1817495 reaction equation
C([O:8][C:9]1[CH:14]=[CH:13][C:12]([C:15]([C:17]2[C:25]3[C:20](=[C:21]([C:26]([F:29])([F:28])[F:27])[CH:22]=[CH:23][CH:24]=3)[N:19]([CH:30]3[CH2:34][CH2:33][CH2:32][CH2:31]3)[N:18]=2)=[O:16])=[CH:11][CH:10]=1)C1C=CC=CC=1>[Pd].C(O)C.C1CCCCC=1>[CH:30]1([N:19]2[C:20]3[C:25](=[CH:24][CH:23]=[CH:22][C:21]=3[C:26]([F:28])([F:29])[F:27])[C:17]([C:15]([C:12]3[CH:11]=[CH:10][C:9]([OH:8])=[CH:14][CH:13]=3)=[O:16])=[N:18]2)[CH2:31][CH2:32][CH2:33][CH2:34]1

Participants

4

Reactant 1

HCID 69064639HCID 69064639, compound

Product 1

HCID 11566962HCID 11566962, compoundYield 81.1%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 18676862Cyclohexene ethanolSolvent

Conditions

Temperature
70 °C

Procedure

A mixture of [4-(benzyloxy)phenyl][1-cyclopentyl-7-(trifluoromethyl)-1H-indazol-3-yl]methanone (0.13 g, 0.28 mmol) and 10% palladium on carbon(0.10 g) in 10 mL ethanol/cyclohexene (3:1, v/v) was heated at 70° C. for 0.5 hours. The catalyst was filtered (celite) and the filtrate concentrated in vacuo to give crude product. The residue was crystallized from Et2O/hexane to give 0.085 g of product as a white solid (mp 225-226° C.).

Workup

  1. filtrationThe catalyst was filtered (celite)
  2. concentrationthe filtrate concentrated in vacuo
  3. customto give crude product
  4. customThe residue was crystallized from Et2O/hexane

Sources & evidence

ORD record
ord-7d56a9407d9a4d2d98879a2e7b56fcc0
Source dataset
uspto-grants-2009_10
Patent number
US07598286B2

Reaction notes

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