반응 #170209

반응 방정식

tert-Butyl acrylate

diisopropylethylamine

P(o-tolyl)3

5-bromo-1H-pyrrolo[2,3-b]pyridine

→

title compound

(E)-tert-Butyl 3-(1H-pyrrolo[2,3-b]pyridin-5-yl)acrylate t-butyl acrylate

용매

propionitrile

dimethylformamide

반응 조건

후처리

1. 1
   기타The resulting mixture was purged with argon
2. 2
   기타The mixture was then purged with argon a second time
3. 3
   온도refluxed overnight
4. 4
   여과The reaction mixture was filtered on Celite®
5. 5
   농축The filtrate was concentrated to dryness
6. 6
   세척The organic layers were washed with a saturated solution of sodium chloride (3×50 mL)
7. 7
   건조dried over sodium sulfate
8. 8
   여과filtered
9. 9
   농축concentrated to dryness
10. 10
    기타The crude was purified by flash chromatography on silica gel

실험 절차

tert-Butyl acrylate (5.9 mL, 40.6 mmol), diisopropylethylamine (3.5 mL, 20.3 mmol) and P(o-tolyl)3 (618 mg, 2.0 mmol) were successively added to a suspension of 5-bromo-1H-pyrrolo[2,3-b]pyridine (2.0 g, 10.15 mmol) in propionitrile (40 mL) and dimethylformamide (10 mL). The resulting mixture was purged with argon prior to the addition of palladium acetate (227 mg, 1.0 mmol). The mixture was then purged with argon a second time and refluxed overnight. The reaction mixture was filtered on Celite®. The filtrate was concentrated to dryness and the residue was solubilized in ethyl acetate (3×100 mL). The organic layers were washed with a saturated solution of sodium chloride (3×50 mL), dried over sodium sulfate, filtered and concentrated to dryness. The crude was purified by flash chromatography on silica gel using dichloromethane/ethyl acetate (1:0 to 7:3) as eluent. The title compound was obtained as a yellow solid (465 mg, 28%)

출처