Water → HCID 21928685, compound

HRID 1243859Notes

Reaction equation

HRID 1243859 reaction equation
[C:1]1([C:7]2([C:21]3[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=3)[CH2:15][C:14]3[C:10](=[C:11]([C:16]([O:18][CH2:19][CH3:20])=[O:17])[NH:12][N:13]=3)[CH:9]=[CH:8]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[H-].[Na+].F[C:30]1[CH:35]=[CH:34][C:33]([N+:36]([O-:38])=[O:37])=[CH:32][CH:31]=1.O>CN(C)C=O>[N+:36]([C:33]1[CH:34]=[CH:35][C:30]([N:13]2[C:14]3[C:10]([CH:9]=[CH:8][C:7]([C:1]4[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=4)([C:21]4[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=4)[CH:15]=3)=[C:11]([C:16]([O:18][CH2:19][CH3:20])=[O:17])[NH:12]2)=[CH:31][CH:32]=1)([O-:38])=[O:37]

Participants

6

Reactant 4

HCID 962WaterHCID 9590p-Fluoronitrobenzene2×HCID 24758Sodium hydrideHCID 178470409HCID 178470409, compound

Product 1

HCID 21928685HCID 21928685, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Conditions

Temperature
80 °C

Procedure

A solution of 1 g of ethyl 6,6-diphenyl-6,7-dihydro-2H-indazole-3-carboxylate in 5 cm3 of dimethylformamide is added dropwise to a suspension of 0.151 g of sodium hydride (at 60% in oil) in 4 cm3 of dimethylformamide. After stirring the mixture for one and a half hours in the region of 20° C., 0.46 cm3 of 1-fluoro-4-nitrobenzene is added and the reaction mixture is stirred in the region of 80° C. for about two hours. A further 0.26 cm3 of 1-fluoro-4-nitrobenzene is added to the mixture, cooled to the region of 20° C. After stirring for two hours in the region of 80° C., the mixture is slowly cooled to the region of 20° C. and 10 cm3 of water are added. The mixture is extracted three times with 75 cm3 of ethyl acetate, and the combined organic phases are washed with twice 75 cm3 of water, 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 (90/10 by volume)], 0.34 g of ethyl 1-(4-nitrophenyl)-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. additionis added
  2. temperaturecooled to the region of 20° C
  3. stirringAfter stirring for two hours in the region of 80° C.
  4. additionare added
  5. extractionThe mixture is extracted three times with 75 cm3 of ethyl acetate
  6. washthe combined organic phases are washed with twice 75 cm3 of water
  7. dry with materialdried over magnesium sulphate
  8. filtrationfiltered
  9. concentrationconcentrated to dryness under reduced pressure (13 kPa)

Sources & evidence

ORD record
ord-c6c763a6de744667867c26cb8d321a67
Source dataset
uspto-grants-2006_10
Patent number
US07119115B2

Reaction notes

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