تفاعل #357203

معادلة التفاعل

solution

tert-butyl 4-[(trifluoroacetyl)oxy]-3,6-dihydropyridine-1(2H)-carboxylate

4-fluorophenylboronic acid

CsF

→

desired product

المردود 78.1%

tert-butyl 4-(4-fluorophenyl)-3,6-dihydropyridine-1(2H)-carboxylate

المردود 78.1%

المذيبات

1,2-dimethoxyethane

methanol

ظروف التفاعل

المعالجة

1. 1
   درجة الحرارةheated
2. 2
   درجة الحرارةto reflux
3. 3
   تركيزThe reaction was concentrated
4. 4
   workup.DISSOLUTIONthe concentrate was dissolved in ethyl acetate (100 mL)
5. 5
   استخلاصThe aqueous layer was extracted with ethyl acetate (2×50 mL)
6. 6
   غسيلthe combined extracts were washed with water and brine
7. 7
   تجفيفdried (Na2SO4)
8. 8
   ترشيحfiltered
9. 9
   تركيزconcentrated
10. 10
    أخرىThe concentrate was purified by flash column chromatography on silica gel with 1:6 ethyl acetate/hexanes

الإجراء التجريبي

A solution of Example 6A (4.0 g, 12 mmol) and 4-fluorophenylboronic acid (1.68 g, 12 mmol) in 1,2-dimethoxyethane (100 mL) and methanol (50 mL) was treated with tetrakis(triphenylphosphine)palladium(0) (0.416 g, 0.36 mmol) and CsF (3.64 g, 24 mmol), heated to reflux, and stirred overnight. The reaction was concentrated and the concentrate was dissolved in ethyl acetate (100 mL) and water (50 mL). The aqueous layer was extracted with ethyl acetate (2×50 mL) and the combined extracts were washed with water and brine, dried (Na2SO4), filtered, and concentrated. The concentrate was purified by flash column chromatography on silica gel with 1:6 ethyl acetate/hexanes to provide the desired product (2.6 g, 78%). MS (CI) m/e 278 (M+H)+.

المصدر