반응 #88497

반응 방정식

Propyne

5-fluoro-3-iodo-pyridin-2-ylamine

triethylamine

→

title compound

수율 84.0%

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

수율 84.0%

용매

THF

THF

반응 조건

후처리

1. 1
   기타condensed into a pre-weighed flask
2. 2
   workup.ADDITIONThe solution was added via cannula to
3. 3
   온도a cooled (0-5° C.)
4. 4
   기타degassed
5. 5
   workup.WAITfor a further 30 minutes at ambient temperature
6. 6
   기타The solid was removed by filtration
7. 7
   세척the cake washed with THF
8. 8
   workup.ADDITIONThe filtrate was diluted with ethyl acetate
9. 9
   추출extracted with 2M hydrochloric acid (×3)
10. 10
    추출The combined acid extract
11. 11
    세척was washed with diethyl ether
12. 12
    workup.ADDITIONmade basic by careful addition of potassium carbonate
13. 13
    추출then extracted with diethyl ether (×3)
14. 14
    건조The combined organic layer was dried (Na2SO4)
15. 15
    여과filtered
16. 16
    기타evaporated

실험 절차

Propyne (15.4 g, 0.39 mol) was condensed into a pre-weighed flask cooled to ca. −40° C. containing THF (80 mL). The solution was added via cannula to a cooled (0-5° C.), degassed mixture of 5-fluoro-3-iodo-pyridin-2-ylamine (61.0 g, 0.26 mol), bis(triphenylphosphine)dichloropalladium(0) (9.0 g, 13.0 mmol), copper (I) iodide (2.95 g, 15.6 mmol) and triethylamine (77.7 g, 107 mL, 0.78 mol) in THF (650 mL). The mixture was stirred at 0-5° C. for 30 minutes then for a further 30 minutes at ambient temperature. The solid was removed by filtration and the cake washed with THF. The filtrate was diluted with ethyl acetate and extracted with 2M hydrochloric acid (×3). The combined acid extract was washed with diethyl ether and then made basic by careful addition of potassium carbonate then extracted with diethyl ether (×3). The combined organic layer was dried (Na2SO4), filtered and evaporated to afford the title compound as a brown solid (32.2 g, 84%). 1H NMR (400 MHz, CDCl3): 7.90 (s, 1H), 7.24 (dd, J=8.4, 2.8 Hz, 1H), 4.84 (s, 2H), 2.11 (s, 3H).

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