HCID 21928685, compound → HCID 21929208, compound

HRID 1243858Notes

Reaction equation

HRID 1243858 reaction equation
[N+:1]([C:4]1[CH:9]=[CH:8][C:7]([N:10]2[C:18]3[C:13]([CH:14]=[CH:15][C:16]([C:25]4[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=4)([C:19]4[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=4)[CH:17]=3)=[C:12]([C:31]([O:33][CH2:34][CH3:35])=[O:32])[NH:11]2)=[CH:6][CH:5]=1)([O-])=O>C(O)(=O)C.[Zn]>[NH2:1][C:4]1[CH:9]=[CH:8][C:7]([N:10]2[C:18]3[C:13]([CH:14]=[CH:15][C:16]([C:19]4[CH:20]=[CH:21][CH:22]=[CH:23][CH:24]=4)([C:25]4[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=4)[CH:17]=3)=[C:12]([C:31]([O:33][CH2:34][CH3:35])=[O:32])[NH:11]2)=[CH:6][CH:5]=1

Participants

4

Reactant 1

HCID 21928685HCID 21928685, compound

Product 1

HCID 21929208HCID 21929208, compoundYield 73%

Reagents, catalysts & solvents 2

HCID 23994ZincCatalystHCID 176Acetic AcidSolvent

Conditions

Temperature
20 °C

Procedure

A solution of 0.6 g of ethyl 1-(4-nitrophenyl)-6,6-diphenyl-1H-indazole-3-carboxylate in 24 cm3 of acetic acid is cooled to the region of 0° C. 4.8 g of zinc are then added portionwise. After warming to a temperature in the region of 20° C., the suspension obtained is stirred for about 4 hours. The insoluble material is filtered off through Celite and washed with three times 10 cm3 of dichloromethane. The filtrate is concentrated to dryness under reduced pressure (13 kPa) and taken up in 50 cm3 of dichloromethane. The solution is washed with three times 20 cm3 of saturated aqueous sodium hydrogen carbonate solution, dried over magnesium sulphate, filtered and concentrated to dryness under reduced pressure (13 kPa). After flash chromatography on a column of silica [eluent: dichloromethane/ethyl acetate (98/2 by volume)], 0.41 g of ethyl 1-(4-aminophenyl)-6,6-diphenyl-1H-indazole-3-carboxylate is thus obtained in the form of a solid, the characteristics of which are as follows:

Workup

  1. customthe suspension obtained
  2. filtrationThe insoluble material is filtered off through Celite
  3. washwashed with three times 10 cm3 of dichloromethane
  4. concentrationThe filtrate is concentrated to dryness under reduced pressure (13 kPa)
  5. washThe solution is washed with three times 20 cm3 of saturated aqueous sodium hydrogen carbonate solution
  6. dry with materialdried over magnesium sulphate
  7. filtrationfiltered
  8. concentrationconcentrated to dryness under reduced pressure (13 kPa)

Sources & evidence

ORD record
ord-4fd8f776ef3a4baeb5e87dcc54274e1c
Source dataset
uspto-grants-2006_10
Patent number
US07119115B2

Reaction notes

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