반응 #600259

반응 방정식

(6-chloro-4-iodo-pyridin-3-yl)-carbamic acid tert-butyl ester

1-butyne

triethylamine

→

tert-butyl 4-(but-1-ynyl)-6-chloropyridin-3-ylcarbamate

수율 74.0%

용매

toluene

water

반응 조건

후처리

1. 1
   여과The solid was filtered off
2. 2
   세척washed with ethyl acetate (60 mL×3)
3. 3
   기타The filtrate was evaporated under reduced pressure
4. 4
   기타the residue was purified by column chromatography on silica gel (petroleum ether/ethyl acetate, 10/1)

실험 절차

To a deoxygenated solution of (6-chloro-4-iodo-pyridin-3-yl)-carbamic acid tert-butyl ester (6.0 g, 16.9 mmol), 1-butyne (9 g, 169 mmol), CuI (160.1 mg, 0.84 mmol) and triethylamine (3.4 g, 33.2 mmol) in toluene (40 mL) and water (14 mL) was added Pd(PPh3)2Cl2 (592 mg, 0.84 mmol) under N2 in a autoclave. The mixture was heated to 70° C. and stirred for 24 h. The solid was filtered off and washed with ethyl acetate (60 mL×3). The filtrate was evaporated under reduced pressure and the residue was purified by column chromatography on silica gel (petroleum ether/ethyl acetate, 10/1) to give tert-butyl 4-(but-1-ynyl)-6-chloropyridin-3-ylcarbamate (3.5 g, 74%). 1H-NMR (CDCl3, 300 MHz) δ 9.13 (s, 1H), 7.22 (s, 1H), 6.98 (s, 1H), 2.53 (q, J=7.5 Hz, 2H), 1.54 (s, 9H), 1.29 (t, J=7.5 Hz, 3H).

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