تفاعل #436007

معادلة التفاعل

methyl-3-bromo-5-[(dipropylamino)carbonyl]benzoate

8-quinolineboronic acid

sodium carbonate

→

methyl 3-[(dipropylamino)carbonyl]-5-(8-quinolinyl)benzoate

المردود 77.7%

المذيبات

water

toluene

ظروف التفاعل

المعالجة

1. 1
   أخرىis degassed under reduced pressure for 15 minutes
2. 2
   أخرىpurged with argon
3. 3
   أخرىthe reaction mixture is degassed under reduced pressure for 15 minutes
4. 4
   أخرىpurged with argon
5. 5
   درجة الحرارةThe reaction mixture is heated
6. 6
   درجة الحرارةat reflux overnight
7. 7
   درجة الحرارةcooled to 20–25 degrees C
8. 8
   workup.ADDITIONand diluted with chloroform
9. 9
   أخرىThe organic phase is separated
10. 10
    غسيلwashed with water (3×50 mL), and saline
11. 11
    تجفيفdried over sodium sulfate
12. 12
    تركيزconcentrated under reduced pressure
13. 13
    أخرىPurification by flash column chromatography (silica, ethyl acetate/hexanes, 1.3/1)

الإجراء التجريبي

A mixture of methyl-3-bromo-5-[(dipropylamino)carbonyl]benzoate (XLVIII, 200 mg, 0.58 mmol), 8-quinolineboronic acid (200.6 mg, 1.2 mmol), sodium carbonate (870 Micro Liter of a 2 M mixture in water, 1.74 mmol) in toluene (6 mL) is degassed under reduced pressure for 15 minutes and purged with argon. Palladium tetrakis(triphenylphosphine) (139 mg, 0.12 mmol) is added and the reaction mixture is degassed under reduced pressure for 15 minutes and purged with argon. The reaction mixture is heated at reflux overnight, cooled to 20–25 degrees C. and diluted with chloroform. The organic phase is separated and washed with water (3×50 mL), and saline, dried over sodium sulfate and concentrated under reduced pressure. Purification by flash column chromatography (silica, ethyl acetate/hexanes, 1.3/1) gives methyl 3-[(dipropylamino)carbonyl]-5-(8-quinolinyl)benzoate (XLIX, 176 mg), NMR (300 MHz, CDCl3): delta 8.91, 8.42, 8.21, 8.09, 7.95, 7.86, 7.77, 7.64, 3.94, 3.49, 3.34, 1.64, 0.99 and 0.84.

المصدر