Water → 5-amino-3-phenethyl-1-(2-trimethylsilanylethoxymethyl)-1H-indazole

HRID 25450Notes

Reaction equation

HRID 25450 reaction equation
[NH2:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[N:7]([CH2:11][O:12][CH2:13][CH2:14][Si:15]([CH3:18])([CH3:17])[CH3:16])[N:6]=[C:5]2[C:19]#[C:20][C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1.O>C(O)C.[Pd]>[NH2:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[N:7]([CH2:11][O:12][CH2:13][CH2:14][Si:15]([CH3:18])([CH3:16])[CH3:17])[N:6]=[C:5]2[CH2:19][CH2:20][C:21]1[CH:22]=[CH:23][CH:24]=[CH:25][CH:26]=1

Participants

5

Reactant 2

HCID 962WaterHCID 686734445-Amino-3-(phenylethynyl)-1-{[2-(trimethylsilyl)ethoxy]methyl}indazole

Product 1

HCID 225671855-amino-3-phenethyl-1-(2-trimethylsilanylethoxymethyl)-1H-indazoleYield 91.2%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

5-Amino-3-phenethyl-1-(2-trimethylsilanylethoxymethyl)-1H-indazole can be obtained in the following way: a solution of 0.9 g of 5-amino-3-phenylethynyl-1-(2-trimethylsilanylethoxymethyl)-1H-indazole in a mixture of 50 ml of absolute ethanol and of 2 ml of water containing 100 mg of 10% palladium-on-charcoal is hydrogenated under a pressure of 1000 kPa at a temperature in the region of 25° C. for 21.5 hours. After filtration of the catalyst through Celite® under argon and washing with ethanol, the filtrate is concentrated to dryness under reduced pressure (2 kPa) at a temperature in the region of 40° C. 0.83 g of crude 5-amino-3-phenethyl-1-(2-trimethylsilanylethoxymethyl)-1H-indazole is thus obtained in the form of a brown-colored oil (CI mass analysis: m/z 368 (M+H)+).

Workup

  1. filtrationAfter filtration of the catalyst through Celite® under argon
  2. washwashing with ethanol
  3. concentrationthe filtrate is concentrated to dryness under reduced pressure (2 kPa) at a temperature in the region of 40° C

Sources & evidence

ORD record
ord-d533b64090314850b540bb416c8cbe86
Source dataset
uspto-grants-2005_02
Patent number
US06858638B2

Reaction notes

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