تفاعل #86317

معادلة التفاعل

NaHCO3

4-bromo-6-(trifluoromethyl)-1H-indazole

methyl 4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)picolinate

→

TFA

title compound

4-(6-(trifluoromethyl)-1H-indazol-4-yl)picolinic acid

المذيبات

dioxane

ظروف التفاعل

المعالجة

1. 1
   أخرىto give a light brown suspension
2. 2
   درجة الحرارةwas then cooled
3. 3
   ترشيحfiltered
4. 4
   تركيزconcentrated in vacuo
5. 5
   أخرىpurified by preparative HPLC (Waters SunFire C18, 5 μm, 30 mm ID×75 mm column)
6. 6
   غسيلeluting with a gradient of 15-55% ACN (containing 0.035% TFA) in water (containing 0.05% TFA)

الإجراء التجريبي

A mixture of 4-bromo-6-(trifluoromethyl)-1H-indazole (0.302 g, 1.140 mmol), methyl 4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)picolinate (0.3 g, 1.140 mmol), and PdCl2(dppf) (0.042 g, 0.057 mmol) in dioxane (10 mL) was combined with aqueous saturated NaHCO3 (3 mL) to give a light brown suspension. The reaction mixture was heated in a microwave reactor at 140° C. for 45 minutes and was then cooled, filtered, concentrated in vacuo, and purified by preparative HPLC (Waters SunFire C18, 5 μm, 30 mm ID×75 mm column) eluting with a gradient of 15-55% ACN (containing 0.035% TFA) in water (containing 0.05% TFA) to give a TFA salt of the title compound. ESI-MS m/z [M+H]+ calc'd for C14H8F3N3O2, 308.1. found 308.1.

المصدر