Reaktion #2155458

Reaktionsgleichung

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

(2-amino-1-phenyl-1H-benzoimidazol-5-yl)methanol

trans-N1,N2-dimethylcyclohexane-1,2-diamine

potassium phosphate

→

product

Ausbeute 7.3%

(2-(5-bromo-1((2-(trimethylsilyl)ethoxy)methyl)-1H-indazol-3-ylamino)-1-phenyl-1H-benzo[d]imidazol-5-yl)methanol

Ausbeute 7.3%

Lösungsmittel

ethyl acetate

tetrahydrofuran

Reaktionsbedingungen

Aufarbeitung

1. 1
   Sonstigeformed
2. 2
   SonstigeThe mixture was then microwaved at 140° C. for 3 hours
3. 3
   Waschenwashed with 5% citric acid, saturated sodium bicarbonate, brine
4. 4
   Trocknendried over magnesium sulfate
5. 5
   Einengenconcentrated
6. 6
   SonstigeThe residue was purified by flash chromatography
7. 7
   Waschenwashed with 1N HCl
8. 8
   Sonstigeto remove residual copper

Vorschrift

A mixture of 5-bromo-3-iodo-1-((2-(trimethylsilyl)ethoxy)methyl)-1H-indazole (906 mg, 0.00200 mol), (2-amino-1-phenyl-1H-benzoimidazol-5-yl)methanol (435 mg, 0.00182 mol), copper(I) iodide (110 mg, 0.00056 mol), trans-N1,N2-dimethylcyclohexane-1,2-diamine (160 mg, 0.0011 mol) and potassium phosphate (772 mg, 0.00364 mol) in tetrahydrofuran (19.4 mL) was stirred under argon sparging until a greenish suspension formed. The mixture was then microwaved at 140° C. for 3 hours. The reaction mixture was diluted with ethyl acetate and washed with 5% citric acid, saturated sodium bicarbonate, brine, dried over magnesium sulfate and concentrated. The residue was purified by flash chromatography using 0-100% ethyl acetate-hexanes. The product was taken up in ethyl acetate, washed with 1N HCl to remove residual copper and rechromatograped to give 75 mg of product.

Quelle