Water → HCID 21928841, compound

HRID 1243833Notes

Reaction equation

HRID 1243833 reaction equation
[CH:1]1([C:4]([C:6]2[C:14]3[CH:13]=[CH:12][C:11]([C:21]4[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=4)([C:15]4[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=4)[CH2:10][C:9]=3[NH:8][N:7]=2)=[O:5])[CH2:3][CH2:2]1.[H-].[Na+].Cl[CH2:30][O:31][CH2:32][CH2:33][Si:34]([CH3:37])([CH3:36])[CH3:35].O>CN(C)C=O>[CH:1]1([C:4]([C:6]2[C:14]3[CH:13]=[CH:12][C:11]([C:21]4[CH:22]=[CH:23][CH:24]=[CH:25][CH:26]=4)([C:15]4[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=4)[CH2:10][C:9]=3[N:8]([CH2:30][O:31][CH2:32][CH2:33][Si:34]([CH3:37])([CH3:36])[CH3:35])[N:7]=2)=[O:5])[CH2:2][CH2:3]1

Participants

6

Reactant 4

HCID 962WaterHCID 24758Sodium hydrideHCID 27242712-Chloromethyl 2-(trimethylsilyl)ethyl etherHCID 21929223HCID 21929223, compound

Product 1

HCID 21928841HCID 21928841, compoundYield 70.9%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent3×

Conditions

Temperature
20 °C

Procedure

A solution of 2.55 g of cyclopropyl(6,6-diphenyl-6,7-dihydro-1H-indazol-3-yl)methanone in 40 cm3 of dimethylformamide is added dropwise at a temperature in the region of 5° C. to a suspension, cooled to this same temperature, of 0.39 g of sodium hydride (at 60% in oil) in 20 cm3 of dimethylformamide. After stirring the mixture at this same temperature for about one and a half hours, a solution of 1.87 g of (2-chloromethoxyethyl)trimethylsilane in 20 cm3 of dimethylformamide is added dropwise without exceeding a temperature of 10° C. After warming to a temperature in the region of 20° C., the mixture is stirred for 2 hours at this same temperature. 20 cm3 of water are then added and the mixture is concentrated under reduced pressure (13 kPa). The residue is taken up in 80 cm3 of water and extracted three times with 60 cm3 of dichloromethane. The combined organic phases are dried over magnesium sulphate, filtered and concentrated to dryness under reduced pressure. After flash chromatography on a column of silica [eluent: dichloromethane/methanol (99/1 by volume)], 2.5 g of cyclopropyl(6,6-diphenyl-1-(2-trimethylsilanylethoxymethyl)-6,7-dihydro-1H-indazol-3-yl)methanone are thus obtained in the form of a solid, the characteristics of which are as follows:

Workup

  1. customa temperature of 10° C
  2. stirringthe mixture is stirred for 2 hours at this same temperature
  3. concentrationthe mixture is concentrated under reduced pressure (13 kPa)
  4. extractionextracted three times with 60 cm3 of dichloromethane
  5. dry with materialThe combined organic phases are dried over magnesium sulphate
  6. filtrationfiltered
  7. concentrationconcentrated to dryness under reduced pressure

Sources & evidence

ORD record
ord-b75bd9f81b124ef48cdb029c385ad35d
Source dataset
uspto-grants-2006_10
Patent number
US07119115B2

Reaction notes

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