HCID 73292041, compound → HCID 73292040, compound

HRID 1398037Notes

Reaction equation

HRID 1398037 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[N+:19]([O-])=O)[N:11]=[C:10]([CH:22]3[CH2:27][C:26]([CH3:29])([CH3:28])[O:25][C:24]([CH3:31])([CH3:30])[CH2:23]3)[CH:9]=2)=[CH:4][CH:3]=1>C(O)C.C(O)(=O)C.[Fe]>[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[NH2:19])[N:11]=[C:10]([CH:22]3[CH2:27][C:26]([CH3:29])([CH3:28])[O:25][C:24]([CH3:31])([CH3:30])[CH2:23]3)[CH:9]=2)=[CH:4][CH:3]=1

Participants

5

Reactant 1

HCID 73292041HCID 73292041, compound

Product 1

HCID 73292040HCID 73292040, compoundYield 98%

Reagents, catalysts & solvents 3

HCID 23925IronCatalystHCID 176Acetic AcidSolventHCID 702EthanolSolvent

Conditions

Temperature
90 °C

Procedure

To a solution of 5-(4-chlorophenyl)-1-(2-nitrophenyl)-3-(2,2,6,6-tetramethyltetrahydro-2H-pyran-4-yl)-1H-pyrazole (Example 61) (1.10 g, 2.50 mmol) in 20 mL of ethanol and 20 mL of acetic acid was added iron powder (1.12 g, 20.0 mmol) and the mixture heated to 90° C. for 1 hr. The mixture was filtered through Celite and concentrated and the residue purified by silica gel chromatography (40-g cartridge, 10-25% EtOAc/heptane) to give 1.0 g (98%) the title compound as a white solid.

Workup

  1. filtrationThe mixture was filtered through Celite
  2. concentrationconcentrated
  3. customthe residue purified by silica gel chromatography (40-g cartridge, 10-25% EtOAc/heptane)

Sources & evidence

ORD record
ord-3673538ff82a4e928b901f14c94049f8
Source dataset
uspto-grants-2014_12
Patent number
US08901314B2

Reaction notes

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