HCID 66974441, compound → HCID 66974561, compound

HRID 1962556Notes

Reaction equation

HRID 1962556 reaction equation
Cl[C:2]1[NH:3][C:4]([C:11]2[CH:16]=[CH:15][C:14]([CH:17]3[CH2:22][CH2:21][CH2:20][CH2:19][CH2:18]3)=[CH:13][CH:12]=2)=[CH:5][C:6]=1[C:7]([O:9][CH3:10])=[O:8].NC1OC(C2C=CC(C3CCCCC3)=CC=2)=CC=1C(OC)=O>CO.C(OCC)(=O)C.[C].[Pd]>[CH:17]1([C:14]2[CH:15]=[CH:16][C:11]([C:4]3[NH:3][CH:2]=[C:6]([C:7]([O:9][CH3:10])=[O:8])[CH:5]=3)=[CH:12][CH:13]=2)[CH2:18][CH2:19][CH2:20][CH2:21][CH2:22]1

Participants

6

Reactant 2

HCID 66974441HCID 66974441, compoundHCID 66974659HCID 66974659, compound

Product 1

HCID 66974561HCID 66974561, compoundYield 41.1%

Reagents, catalysts & solvents 3

HCID 178418390HCID 178418390, compoundCatalystHCID 887MethanolSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
50 °C

Procedure

To a solution of a nearly 1:1 mixture (3.41 g) of methyl 2-chloro-5-(4-cyclohexylphenyl)-1H-pyrrole-3-carboxylate and methyl 2-amino-5-(4-cyclohexylphenyl)-3-furoate in methanol (30 mL) and ethyl acetate (10 mL) was added 10% palladium carbon (50% containing water, 0.34 g), and the mixture was stirred under a hydrogen atmosphere at 50° C. for 14 hr. The reaction mixture was filtered, and the filtrate was concentrated under reduced pressure. The residue was purified by silica gel column chromatography (eluent: hexane-ethyl acetate=3:1→2:1) to give the title compound as crystals (yield 1.25 g, 41%).

Workup

  1. filtrationThe reaction mixture was filtered
  2. concentrationthe filtrate was concentrated under reduced pressure
  3. customThe residue was purified by silica gel column chromatography (eluent: hexane-ethyl acetate=3:1→2:1)

Sources & evidence

ORD record
ord-06c4055144af4b37a75ffce3664881d6
Source dataset
uspto-grants-2013_04
Patent number
US08415368B2

Reaction notes

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