Reacción #332819

Ecuación de reacción

6-amino-3-bromo-5-chloro-1H-indazole-7-carboxylic acid methyl ester

9-methoxy-9-bora-bicyclo[3.3.1]nonane

methyl lithium

→

product

Rendimiento 66.0%

6-amino-5-chloro-3-methyl-1H-indazole-7-carboxylic acid methyl ester

Rendimiento 66.0%

Disolventes

tetrahydrofuran

tetrahydrofuran

diethylether

Condiciones de reacción

Tratamiento posterior

1. 1
   workup.ADDITIONis added
2. 2
   workup.STIRRINGThe reaction mixture is stirred in a microwave oven at 150° C. for 15 minutes
3. 3
   FiltraciónAfter filtration
4. 4
   Concentraciónover Celite and concentration in vacuo
5. 5
   Otrothe residue is purified by flash chromatography (SiO2, hexanes/ethyl acetate 1:1)

Procedimiento

To a solution of 899 mg (5.91 mmol) of 9-methoxy-9-bora-bicyclo[3.3.1]nonane in 5 mL of anhydrous tetrahydrofuran is added dropwise 3.71 mL (5.91 mmol) of a solution 1N of methyl lithium in diethylether. After few minutes of stirring, a mixture of 6-amino-3-bromo-5-chloro-1H-indazole-7-carboxylic acid methyl ester, prepared as in step a in example 39, and 104 mg (0.15 mmol) of bis(triphenylphosphine) palladiumI(II) dichloride in 10 mL of anhydrous tetrahydrofuran is added. The reaction mixture is stirred in a microwave oven at 150° C. for 15 minutes. After filtration over Celite and concentration in vacuo, the residue is purified by flash chromatography (SiO2, hexanes/ethyl acetate 1:1) to afford 470 mg of product (66%) as a pale yellowish solid; LC/MS:240/242 (M+H)+.

Fuente