反応 #57209

反応方程式

phenyl isocyanate

[3-(4-nitrophenyl)-4-(1H-pyrrolo[2,3-b]pyridin-4-yl)-1H-pyrazol-1-yl]acetic acid

tin

hydrochloric acid

→

title compound

収率 93.0%

[3-(4-{[(phenylamino)carbonyl]amino}phenyl)-4-(1H-pyrrolo[2,3-b]pyridin-4-yl)-1H-pyrazol-1-yl]acetic acid

収率 93.0%

溶媒

ethanol

反応条件

後処理

1. 1
   ろ過The solution was filtered through Celite
2. 2
   濃縮concentrated in vacuo
3. 3
   workup.DISSOLUTIONThe resulting aniline was dissolved in anhydrous pyridine (10 mL)
4. 4
   workup.STIRRINGThe reaction mixture was stirred at room temperature for 4 h
5. 5
   濃縮After concentration
6. 6
   その他in vacuo, purification by Gilson reverse phase HPLC

実験手順

A heterogeneous mixture of [3-(4-nitrophenyl)-4-(1H-pyrrolo[2,3-b]pyridin-4-yl)-1H-pyrazol-1-yl]acetic acid (31.0 mmol), elemental tin dust (5.30 mmol), 6.0N aqueous hydrochloric acid (5.3 mL) and absolute ethanol (5.3 mL) was stirred at 70° C. for 1 h. The solution was filtered through Celite and concentrated in vacuo. The resulting aniline was dissolved in anhydrous pyridine (10 mL) and phenyl isocyanate (11.17 mmol) added dropwise. The reaction mixture was stirred at room temperature for 4 h. After concentration in vacuo, purification by Gilson reverse phase HPLC afforded the title compound as a white solid (93%). ESMS [M+H]+: 453.2

出典