반응 #77849

반응 방정식

ethyl acetate

2,5-dibromopyridine

N-Boc-propargylamine

N-Cbz-propargylamine

→

6-1

수율 11.9%

Benzyl 3-(6-{3-[(tert-butoxycarbonyl)amino]prop-1-ynyl}pyridin-3-yl)prop-2-ynylcarbamate

수율 11.9%

용매

diisopropylamine

반응 조건

후처리

1. 1
   온도the mixture was heated
2. 2
   온도under reflux temperature for 5 hours under nitrogen atmosphere
3. 3
   온도The mixture was cooled to room temperature
4. 4
   여과The precipitates were filtered
5. 5
   세척washed with ethyl acetate
6. 6
   기타purified by silica gel column

실험 절차

A mixture of 2,5-dibromopyridine (1.19 g), N-Boc-propargylamine (781 mg), Pd(PPh3)2Cl2 (73 mg), and CuI (10 mg) in diisopropylamine (20 mL) was stirred at room temperature overnight under nitrogen atmosphere. To the mixture was added N-Cbz-propargylamine (1.14 g) and the mixture was heated under reflux temperature for 5 hours under nitrogen atmosphere. The mixture was cooled to room temperature. To the mixture was added ethyl acetate (50 mL). The precipitates were filtered and washed with ethyl acetate. The filtrate and washings were combined and purified by silica gel column to give 6-1 (250 mg) as a crystalline compound.

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