HCID 73291873, compound → HCID 73291872, compound

HRID 1398045Notes

Reaction equation

HRID 1398045 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[N:12]([C:13]3[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=3[O:19][CH3:20])[N:11]=[C:10]([C:21]3[C:22]([CH3:29])([CH3:28])[O:23][C:24]([CH3:27])([CH3:26])[CH:25]=3)[CH:9]=2)=[CH:4][CH:3]=1>C(OCC)(=O)C.O=[Pt]=O>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[N:12]([C:13]3[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=3[O:19][CH3:20])[N:11]=[C:10]([CH:21]3[CH2:25][C:24]([CH3:27])([CH3:26])[O:23][C:22]3([CH3:29])[CH3:28])[CH:9]=2)=[CH:4][CH:3]=1

Participants

4

Reactant 1

HCID 73291873HCID 73291873, compound

Product 1

HCID 73291872HCID 73291872, compoundYield 42.6%

Reagents, catalysts & solvents 2

HCID 345198Adams' catalystCatalyst2×HCID 8857Ethyl AcetateSolvent

Procedure

A solution of 5-(4-chlorophenyl)-1-(2-methoxyphenyl)-3-(2,2,5,5-tetramethyl-2,5-dihydrofuran-3-yl)-1H-pyrazole (162 mg, 0.4 mmol, 1 eq) (Example 67) and PtO2 (9 mg, 0.04 mmol, 0.1 eq) in ethyl acetate (10 mL) was put under a balloon of H2 and stirred overnight. Additional PtO2 (9 mg) was then added and the reaction stirred for 3 more days under a balloon of H2. The reaction was filtered through Celite, and concentrated. Purification by HPLC eluting with 30 to 100% acetonitrile/H2O gave the title compound (70 mg, 41%).

Workup

  1. stirringthe reaction stirred for 3 more days under a balloon of H2
  2. filtrationThe reaction was filtered through Celite
  3. concentrationconcentrated
  4. customPurification by HPLC
  5. washeluting with 30 to 100% acetonitrile/H2O

Sources & evidence

ORD record
ord-aa71de9cc57042fca2aebca87bed08b5
Source dataset
uspto-grants-2014_12
Patent number
US08901314B2

Reaction notes

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