반응 #88506

반응 방정식

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

potassium tert-butoxide

→

title compound

수율 84.0%

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

수율 84.0%

용매

tert-butanol

반응 조건

후처리

1. 1
   온도to cool to ambient temperature
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
   여과filtered
9. 9
   기타evaporated
10. 10
    기타then triturated with diethyl ether

실험 절차

5-Chloro-3-prop-1-ynyl-pyridin-2-ylamine (53.7 g, 0.32 mol) was treated with a 1M solution of potassium tert-butoxide in tert-butanol (515 mL) and the reaction mixture was heated at 85° C. 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), filtered and evaporated then triturated with diethyl ether to afford the title compound as a grey solid (44.8 g, 83%). LCMS (Method B): RT=3.64 min, M+H+=167/169. 1H NMR (400 MHz, DMSO-d6): 8.02 (d, J=2.4 Hz, 1H), 7.83 (d, J=2.4 Hz, 1H), 6.11 (d, J=1.1 Hz, 1H), 2.40 (d, J=1.0 Hz, 3H).

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