Reaktion #2155463

Reaktionsgleichung

ethyl 2-amino-1-(trans-4-(tert-butyldimethylsilyloxy)cyclohexyl)-1H-benzo[d]imidazole-5-carboxylate

5-bromo-3-iodo-1-((2-(trimethylsilyl)ethoxy)methyl)-1H-indazole

1,4-dioxane

potassium phosphate

xantphos

→

oil

Ausbeute 54.7%

Ethyl 2-(5-bromo-1-((2-(trimethylsilyl)ethoxy)methyl)-1H-indazol-3-ylamino)-1-(trans-4-(tert-butyldimethylsilyloxy)cyclohexyl)-1H-benzo[d]imidazole-5-carboxylate

Ausbeute 54.7%

Reaktionsbedingungen

Aufarbeitung

1. 1
   Sonstigewas placed in a microwave reaction vessel
2. 2
   Waschenthe sides were washed down with additional 1,4-dioxane (0.5 mL)
3. 3
   SonstigeThe reaction vessel was irradiated under microwave radiation for 60 minutes at 130° C
4. 4
   workup.ADDITIONThe reaction mixture was diluted with ethyl acetate
5. 5
   Waschenwashed with aqueous saturated sodium bicarbonate
6. 6
   TrocknenThe organic phase was dried over sodium sulfate
7. 7
   Einengenconcentrated to a brown residue which
8. 8
   Sonstigewas purified by combiflash chromatography on a 40 g silica gel cartridge
9. 9
   Sonstigefor 5 minutes
10. 10
    Sonstigeover the next 15 minutes

Vorschrift

A mixture of ethyl 2-amino-1-(trans-4-(tert-butyldimethylsilyloxy)cyclohexyl)-1H-benzo[d]imidazole-5-carboxylate (102 mg, 0.000244 mol), 5-bromo-3-iodo-1-((2-(trimethylsilyl)ethoxy)methyl)-1H-indazole (130 mg, 0.00029 mol), 1,4-dioxane (0.6 mL, 0.007 mol), potassium phosphate (78 mg, 0.00037 mol), xantphos (34 mg, 0.000059 mol) and tris(dibenzylideneacetone)dipalladium(0) (20 mg, 0.00002 mol) was placed in a microwave reaction vessel. The reaction mixture was stirred under nitrogen and the sides were washed down with additional 1,4-dioxane (0.5 mL). The reaction vessel was irradiated under microwave radiation for 60 minutes at 130° C. The reaction mixture was diluted with ethyl acetate and washed with aqueous saturated sodium bicarbonate and then brine. The organic phase was dried over sodium sulfate and concentrated to a brown residue which was purified by combiflash chromatography on a 40 g silica gel cartridge using an initial eluent of 10% ethyl acetate-90% hexanes for 5 minutes then a gradient to 30% ethyl acetate over the next 15 minutes. Concentration of the product fractions gave a yellow oil (99.1 mg).

Quelle