反応 #2439963

ord-e63f3380b8dc4a3a9de0082715bfda43

反応方程式

Cl
HCl
CCn1nc(C)cc1C(=O)Nc1ccc(Cc2ccc3c(c2)CC(=O)N3)cc1
2-Ethyl-5-methyl-2H-pyrazole-3-carboxylic acid [4-(2-oxo-2,3-dihydro-1H-indol-5-ylmethyl)-phenyl]-amide
CCOC=O
ethyl formate
CC[O-].[Na+]
sodium ethoxide
CCn1nc(C)cc1C(=O)Nc1ccc(Cc2ccc3c(c2)C(=CO)C(=O)N3)cc1
product
収率 47.0%
CCn1nc(C)cc1C(=O)Nc1ccc(Cc2ccc3c(c2)C(=CO)C(=O)N3)cc1
2-Ethyl-5-methyl-2H-pyrazole-3-carboxylic acid [4-(3-hydroxymethylene-2-oxo-2,3-dihydro-1H-indol-5-ylmethyl)-phenyl]-amide
収率 47.0%

反応条件

温度
78°CELSIUS
詳細条件
See reaction.notes.procedure_details.

後処理

  1. 1
    その他producing a viscous, dark reddish colored oil
  2. 2
    温度Subsequently, the reaction mixture was cooled to room temperature
  3. 3
    ろ過The suspension was filtered

実験手順

2-Ethyl-5-methyl-2H-pyrazole-3-carboxylic acid [4-(2-oxo-2,3-dihydro-1H-indol-5-ylmethyl)-phenyl]-amide (0.140 g, 0.374 mmol) and ethyl formate (0.060 mL, 0.816 mmol) were dissolved in anhydrous ethanol (0.250 mL). The resulting solution was treated in dropwise fashion with a 21 wt % solution of sodium ethoxide in ethanol (0.42 mL, 1.12 mmol). This reaction mixture was heated at 78° C. for 0.5-1 h, producing a viscous, dark reddish colored oil. Subsequently, the reaction mixture was cooled to room temperature, and then the reaction pH was adjusted to pH 3 with dropwise addition of 1M HCl(aq) causing the formation of a grey precipitate. The suspension was filtered yielding a grey solid as the pure product (0.070 g, 0.175 mmol, 47%).

出典

DOI: 10.6084/m9.figshare.5104873.v1特許: US07749530B2uspto-grants-2010_07