反応 #170209

反応方程式

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

溶媒

propionitrile

dimethylformamide

反応条件

後処理

1. 1
   その他The resulting mixture was purged with argon
2. 2
   その他The mixture was then purged with argon a second time
3. 3
   温度refluxed overnight
4. 4
   ろ過The reaction mixture was filtered on Celite®
5. 5
   濃縮The filtrate was concentrated to dryness
6. 6
   洗浄The organic layers were washed with a saturated solution of sodium chloride (3×50 mL)
7. 7
   乾燥dried over sodium sulfate
8. 8
   ろ過filtered
9. 9
   濃縮concentrated to dryness
10. 10
    その他The crude was purified by flash chromatography on silica gel

実験手順

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%)

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