반응 #88490

반응 방정식

5-Bromo-3-prop-1-ynyl-pyridin-2-ylamine

potassium tert-butoxide

→

title compound

수율 97.5%

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

수율 97.5%

용매

tert-butanol

반응 조건

후처리

1. 1
   온도the reaction mixture was heated at 85 OC for 1 hour
2. 2
   여과The resultant precipitate was collected by filtration
3. 3
   세척washed with water
4. 4
   workup.WAITleft to air
5. 5
   기타dry
6. 6
   workup.DISSOLUTIONThe resultant solid was dissolved in dichloromethane
7. 7
   건조dried (Na2SO4)
8. 8
   기타evaporated
9. 9
   기타then triturated with diethyl ether

실험 절차

5-Bromo-3-prop-1-ynyl-pyridin-2-ylamine (91 g, 431 mmol) was treated with a 1M solution of potassium tert-butoxide in tert-butanol (700 mL) and the reaction mixture was heated at 85 OC for 1 hour. The mixture was then allowed to cool to ambient temperature and poured onto a 1:1 mixture of water/ice (ca. 1 L). The resultant precipitate was collected by filtration, washed with water and left to air dry. The resultant solid was dissolved in dichloromethane, dried (Na2SO4) and evaporated then triturated with diethyl ether to afford the title compound as a brown solid (88.7 g, 97%). 1H NMR (400 MHz, CDCl3): 10.21 (s, 1H), 8.22 (d, J=2.1 Hz, 1H), 7.91 (d, J=2.1 Hz, 1H), 6.13 (s, 1H), 2.52 (s, 3H).

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