تفاعل #452702

معادلة التفاعل

ethyl 4-bromobenzoate

(1-isopropyl-4,4,7-trimethyl-1,2,3,4-tetrahydroquinolin-6-yl)amine

Compound 19

(1-isopropyl-4,4,7-trimethyl-1,2,3,4-tetrahydroquinolin-6-yl)amine

cesium carbonate

→

title compound

المردود 56.0%

Ethyl [(1-isopropyl-4,4,7-trimethyl-1,2,3,4-tetrahydroquinolin-6-yl)amino)benzoate

المردود 56.0%

المذيبات

water

toluene

ظروف التفاعل

المعالجة

1. 1
   درجة الحرارةThe reaction mixture was then cooled to room temperature
2. 2
   استخلاصextracted with ethyl ether (2×)
3. 3
   غسيلThe combined organic extracts were washed with brine
4. 4
   تجفيفdried (MgSO4)
5. 5
   تركيزThe filtered solution was concentrated under reduced pressure
6. 6
   أخرىthe crude product was purified by silica gel chromatography (10% ethyl acetate in hexanes)

الإجراء التجريبي

To a solution of ethyl 4-bromobenzoate (0.98 g, 4.3 mmol) and (1-isopropyl-4,4,7-trimethyl-1,2,3,4-tetrahydroquinolin-6-yl)amine (Compound 19, 0.69 g, 3.0 mmol) in 15.0 mL of toluene stirring under argon was added cesium carbonate (1.84 g, 5.6 mmol), tris(dibenzylideneacetone)dipalladium(0) (35 mg, 0.04 mmol) and BINAP (68 mg, 0.11 mmol) consecutively. The reaction mixture was then heated at 100° C. for 48 hours. The reaction mixture was then cooled to room temperature, diluted with water and extracted with ethyl ether (2×). The combined organic extracts were washed with brine and dried (MgSO4). The filtered solution was concentrated under reduced pressure and the crude product was purified by silica gel chromatography (10% ethyl acetate in hexanes) to give the title compound (0.63 g, 56% 2 steps) as an orange solid.

المصدر