反応 #584768

反応方程式

crotonyl chloride

6-chloro-1H-indazole-3-amine

→

solid

N-(6-chloro-1H-indazol-3-yl)-2-butenamide

溶媒

pyridine

反応条件

後処理

1. 1
   workup.WAITto rise to about 19° C. over 22 hours
2. 2
   濃縮The reaction medium is then concentrated to dryness under reduced pressure (2 kPa; 40° C.)
3. 3
   洗浄The organic phase is washed with 2×50 cm3 of distilled water
4. 4
   乾燥The resulting solution is dried over magnesium sulphate
5. 5
   ろ過filtered through a sinter funnel
6. 6
   その他evaporated under the conditions
7. 7
   その他The residue obtained
8. 8
   その他is purified by chromatography under an argon pressure of 50 kPa
9. 9
   洗浄on a column of silica gel (particle size 40-60 μm; diameter 4.5 cm), eluting with a cyclohexane/ethyl acetate mixture (80/20 by volume)
10. 10
    その他collecting 20 cm3 fractions
11. 11
    workup.ADDITIONThe fractions containing the expected product
12. 12
    その他evaporated under the conditions
13. 13
    乾燥After drying (90 Pa; 45° C.), 100 mg of N-(6-chloro-1H-indazol-3-yl)-2-butenamide, E form

実験手順

0.67 cm3 of distilled crotonyl chloride is added to 50 mg of 6-chloro-1H-indazole-3-amine dissolved in 5 cm3 of pyridine and cooled to about 6° C. The mixture is stirred for 10 minutes and the temperature is then allowed to rise to about 19° C. over 22 hours. The reaction medium is then concentrated to dryness under reduced pressure (2 kPa; 40° C.) and the residue is then taken up in 50 cm3 of tetrahydrofuran and 25 cm3 of ethyl acetate. The organic phase is washed with 2×50 cm3 of distilled water and then with 50 cm3 of saturated aqueous sodium chloride solution. The resulting solution is dried over magnesium sulphate, filtered through a sinter funnel and then evaporated under the conditions described previously. The residue obtained is purified by chromatography under an argon pressure of 50 kPa, on a column of silica gel (particle size 40-60 μm; diameter 4.5 cm), eluting with a cyclohexane/ethyl acetate mixture (80/20 by volume) and collecting 20 cm3 fractions. The fractions containing the expected product are combined and then evaporated under the conditions already described. After drying (90 Pa; 45° C.), 100 mg of N-(6-chloro-1H-indazol-3-yl)-2-butenamide, E form, are obtained in the form of a white solid melting at 226° C.

出典