反応 #77847

反応方程式

2,5-dibromopyridine

N-Cbz-propargylamine

→

7-1

収率 73.8%

Benzyl 3-(5-bromopyridin-2-yl)prop-2-ynylcarbamate

収率 73.8%

溶媒

diisopropylamine

ethyl acetate

反応条件

後処理

1. 1
   ろ過The mixture was filtered
2. 2
   洗浄washed with ethyl acetate (20 mL)
3. 3
   洗浄The filtrate and wash
4. 4
   濃縮concentrated under reduced pressure
5. 5
   その他triturated in MTBE

実験手順

A mixture of 2,5-dibromopyridine (1.19 g), N-Cbz-propargylamine (1.04 g), Pd(PPh3)2Cl2 (73 mg), and CuI (10 mg) in diisopropylamine (20 mL) was stirred at ambient temperature for 3 hours under nitrogen. The mixture was diluted with ethyl acetate (50 mL). The mixture was filtered and washed with ethyl acetate (20 mL). The filtrate and wash were combined, concentrated under reduced pressure and triturated in MTBE to give crystalline 7-1 (1.28 g). The mother liquor was further purified by silica gel column chromatography using a mixture of MTBE: hexanes (1:1) to give an additional 280 mg of 7-1.

出典