تفاعل #166578

معادلة التفاعل

tricyclohexyl phosphine

3-bromo-1-((1-isopropyl-1H-pyrazol-3-yl)methyl)-4-nitro-1H-indazole

cyclopropylboronic acid

potassium phosphate

→

3-cyclopropyl-1-((1-isopropyl-1H-pyrazol-3-yl)methyl)-4-nitro-1H-indazole

المردود 67.2%

المذيبات

toluene water

ظروف التفاعل

المعالجة

1. 1
   أخرىThe mixture was degassed for 30 minutes with an argon filled balloon
2. 2
   workup.ADDITIONPalladium acetate was added (55.5 mg, 0.247 mmol)
3. 3
   أخرىThe mixture was further degassed with argon
4. 4
   ترشيحThe mixture was filtered through GF/F paper
5. 5
   غسيلrinsing with EtOAc
6. 6
   تركيزconcentrated under vacuum
7. 7
   أخرىthe residue was purified by silica gel chromatography (1-20% EtOAc in hexanes)

الإجراء التجريبي

A flask was charged with 3-bromo-1-((1-isopropyl-1H-pyrazol-3-yl)methyl)-4-nitro-1H-indazole (1.8 g, 4.94 mmol), cyclopropylboronic acid (0.849 g, 9.88 mmol), potassium phosphate (3.15 g, 14.8 mmol) and 20:1 toluene/water (10.5 mL). The mixture was degassed for 30 minutes with an argon filled balloon. Palladium acetate was added (55.5 mg, 0.247 mmol) followed by tricyclohexyl phosphine (0.139 g, 0.494 mmol). The mixture was further degassed with argon and heated at 100-110° C. for 16 hours. The mixture was filtered through GF/F paper, rinsing with EtOAc, concentrated under vacuum and the residue was purified by silica gel chromatography (1-20% EtOAc in hexanes) to provide 3-cyclopropyl-1-((1-isopropyl-1H-pyrazol-3-yl)methyl)-4-nitro-1H-indazole (1.08 g, 67% yield) as a yellow solid.

المصدر