تفاعل #88422

معادلة التفاعل

sodium hydrogen carbonate

Cyclopropylboronic acid

tricyclohexylphosphine

methyl 4-(5-bromo-4-(difluoromethyl)thiazol-2-yl)-1-methyl-1H-pyrazole-5-carboxylate

→

title compound

المردود 83.0%

methyl 4-(5-cyclopropyl-4-(difluoromethyl)thiazol-2-yl)-1-methyl-1H-pyrazole-5-carboxylate

المردود 83.0%

المذيبات

ethyl acetate

toluene

water

ظروف التفاعل

المعالجة

1. 1
   أخرىobtained in (Example 1.4) <Step 1>
2. 2
   استخلاصAfter extraction of organic layers, water layers
3. 3
   استخلاصwere extracted with ethyl acetate (50 ml)
4. 4
   غسيلThe combined organic layer was washed with a saturated saline
5. 5
   تجفيفwas then dried over anhydrous sodium sulfate
6. 6
   workup.DISTILLATIONThe solvent was distilled away under reduced pressure
7. 7
   أخرىthe obtained residue was then purified by silica gel column chromatography (silica gel:eluent; heptane:ethyl acetate=93:7-40:60)

الإجراء التجريبي

Cyclopropylboronic acid (61 mg), palladium acetate (11 mg), phosphoric acid potassium salts (203 mg), water (0.53 ml), and tricyclohexylphosphine (27 mg) were added to a toluene (6 ml) solution of the methyl 4-(5-bromo-4-(difluoromethyl)thiazol-2-yl)-1-methyl-1H-pyrazole-5-carboxylate (84 mg) obtained in (Example 1.4) <Step 1>, and the obtained mixture was then stirred in a nitrogen atmosphere at 100° C. for 1.5 hours. Thereafter, ethyl acetate (50 ml) and a saturated sodium hydrogen carbonate aqueous solution (30 ml) were added to the reaction solution. After extraction of organic layers, water layers were extracted with ethyl acetate (50 ml). The organic layers were combined. The combined organic layer was washed with a saturated saline, and was then dried over anhydrous sodium sulfate. The solvent was distilled away under reduced pressure, and the obtained residue was then purified by silica gel column chromatography (silica gel:eluent; heptane:ethyl acetate=93:7-40:60), so as to obtain the title compound (62 mg) in the form of a light brown solid.

المصدر