تفاعل #88423

معادلة التفاعل

(E)-2-(2-ethoxyvinyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane

tripotassium phosphate

2-dicyclohexylphosphino-2′,6′-dimethoxy-1,1′-biphenyl

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

sodium hydrogen carbonate

→

title compound

المردود 63.8%

(E)-methyl 4-(5-(2-ethoxyvinyl)-4-methylthiazol-2-yl)-1-methyl-1H-pyrazole-5-carboxylate

المردود 63.8%

المذيبات

acetonitrile

water

ethyl acetate

ظروف التفاعل

المعالجة

1. 1
   أخرىobtained in (Example 5.11) <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=92:8-40:60)

الإجراء التجريبي

(E)-2-(2-ethoxyvinyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane (63 mg), palladium acetate (7.1 mg), tripotassium phosphate (67 mg), 2-dicyclohexylphosphino-2′,6′-dimethoxy-1,1′-biphenyl (26 mg), and water (0.35 ml) were added to an acetonitrile (4.0 ml) solution of the methyl 4-(5-bromo-4-methylthiazol-2-yl)-1-methyl-1H-pyrazole-5-carboxylate (50 mg) obtained in (Example 5.11) <Step 1>, and the obtained mixture was then stirred under heating in a nitrogen atmosphere for 2 hours at 90° C. 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=92:8-40:60), so as to obtain the title compound (31 mg) in the form of a yellow solid.

المصدر