تفاعل #74602

معادلة التفاعل

2-bromo-1-methoxy-4-(trifluoromethyl)benzene

tert-butyl 4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-3,6-dihydropyridine-1(2H)-carboxylate

potassium carbonate

dichloromethane

→

title compound

tert-Butyl 4-[2-methoxy-5-(trifluoromethyl)phenyl]-3,6-dihydropyridine-1(2H)-carboxylate

المذيبات

N,N-dimethylformamide

ظروف التفاعل

المعالجة

1. 1
   أخرىwas purged with argon
2. 2
   درجة الحرارةbefore cooling to room temperature
3. 3
   ترشيحfiltering through Celite™
4. 4
   غسيلwashing with ethyl acetate
5. 5
   تركيزThe filtrate was concentrated in vacuo to ˜quarter
6. 6
   أخرىpartitioned between water (100 mL) and ethyl acetate (75 mL)
7. 7
   استخلاصThe aqueous layer was extracted with ethyl acetate (2×75 mL)
8. 8
   غسيلCombined organic layers were washed with water, aqueous lithium chloride solution, saturated aqueous sodium chloride solution
9. 9
   تجفيفdried over sodium sulfate
10. 10
    ترشيحfiltered
11. 11
    تركيزconcentrated in vacuo
12. 12
    أخرىThe residue was purified by automated flash chromatography (24 g silica gel)
13. 13
    غسيلeluting with hexanes

الإجراء التجريبي

A suspension of 2-bromo-1-methoxy-4-(trifluoromethyl)benzene (825 mg, 3.23 mmol), tert-butyl 4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-3,6-dihydropyridine-1(2H)-carboxylate (1.00 g, 3.23 mmol), potassium carbonate (1.34 g, 9.697 mmol) and [1,1-bis(diphenylphosphino)ferrocene]dichloro-palladium(11) complex with dichloromethane (1:1) (158 mg, 0.193 mmol) in N,N-dimethylformamide (19 mL) was purged with argon. After 30 minutes, the reaction mixture was heated at 90° C. and stirred for 22 hours before cooling to room temperature and filtering through Celite™, washing with ethyl acetate. The filtrate was concentrated in vacuo to ˜quarter and partitioned between water (100 mL) and ethyl acetate (75 mL). The aqueous layer was extracted with ethyl acetate (2×75 mL). Combined organic layers were washed with water, aqueous lithium chloride solution, saturated aqueous sodium chloride solution, dried over sodium sulfate, filtered and concentrated in vacuo. The residue was purified by automated flash chromatography (24 g silica gel) eluting with hexanes:ethyl acetate (gradient 1:0 to 3:1, by volume) to afford the title compound as a clear oil, 1.1 g.

المصدر