反应详情

0.89 ml (11.8 mmol) of methanesulfonyl chloride was added dropwise while stirring to a solution, cooled to 0°, of 1.52 g (5.88 mmol) of (RS)-1-(4,5-dihydro-8-methoxy-1H-benz[g]indazol-1-yl)-propan-2-ol and 3.27 ml (23.5 mmol) of triethylamine in 60 ml of dichloromethane and the mixture was stirred at this temperature for a further 1.5 hours. The reaction mixture was subsequently diluted with 100 ml of dichloromethane, washed twice with 50 ml of saturated sodium hydrogen carbonate solution each time and the combined aqueous phases were extracted once with 50 ml of dichloromethane. The combined organic phases were washed with 50 ml of saturated sodium chloride solution, dried over magnesium sulfate and evaporated in a vacuum. The brown oil obtained was dissolved in 50 ml of anhydrous dimethylformamide, treated with 0.76 g (11.8 mmol) of sodium azide and the reaction mixture was heated to 85° for 15 hours while stirring. After cooling, the solution was poured into 80 ml of semi-saturated sodium chloride solution and extracted twice with 80 ml of diethyl ether each time. The combined organic phases were washed once with 80 ml of water and once with 80 ml of saturated sodium chloride solution, dried over magnesium sulfate and the solution was concentrated in a vacuum. The brown oil obtained was purified by column chromatography on silica gel (ethyl acetate/toluene 1:1). 1 g (60%) of (RS)-1-(2-azido-propyl)-4,5-dihydro-8-methoxy-1H-benz[g]indazole was obtained as a light yellow oil.

1. stirringthe mixture was stirred at this temperature for a further 1.5 hours
2. washwashed twice with 50 ml of saturated sodium hydrogen carbonate solution each time
3. extractionthe combined aqueous phases were extracted once with 50 ml of dichloromethane
4. washThe combined organic phases were washed with 50 ml of saturated sodium chloride solution
5. dry with materialdried over magnesium sulfate
6. customevaporated in a vacuum
7. customThe brown oil obtained
8. temperaturethe reaction mixture was heated to 85° for 15 hours
9. stirringwhile stirring
10. temperatureAfter cooling
11. extractionextracted twice with 80 ml of diethyl ether each time
12. washThe combined organic phases were washed once with 80 ml of water and once with 80 ml of saturated sodium chloride solution
13. dry with materialdried over magnesium sulfate
14. concentrationthe solution was concentrated in a vacuum
15. customThe brown oil obtained
16. customwas purified by column chromatography on silica gel (ethyl acetate/toluene 1:1)