تفاعل #2439950

ord-eb7c8ca6f89b47929d179b107561a467

معادلة التفاعل

Cl
HCl
CCn1nc(C)cc1C(=O)Nc1ccc(C(=O)c2ccc3c(c2)CC(=O)N3)cc1
2-Ethyl-5-methyl-2H-pyrazole-3-carboxylic acid [4-(2-oxo-2,3-dihydro-1H-indole-5-carbonyl)-phenyl]-amide
CCOC=O
ethyl formate
CC[O-].[Na+]
sodium ethoxide
CCn1nc(C)cc1C(=O)Nc1ccc(C(=O)c2ccc3c(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-indole-5-carbonyl)-phenyl]-amide
المردود 75.1%

المذيبات

ظروف التفاعل

درجة الحرارة
78°CELSIUS
الظروف التفصيلية
See reaction.notes.procedure_details.

المعالجة

  1. 1
    أخرىproducing a black oil
  2. 2
    درجة الحرارةSubsequently, the reaction mixture was cooled to room temperature
  3. 3
    ترشيحThe suspension was filtered

الإجراء التجريبي

2-Ethyl-5-methyl-2H-pyrazole-3-carboxylic acid [4-(2-oxo-2,3-dihydro-1H-indole-5-carbonyl)-phenyl]-amide (0.735 g, 1.89 mmol) and ethyl formate (0.454 mL, 3.78 mmol) were dissolved in anhydrous ethanol (3.80 mL). The resulting solution was treated in dropwise fashion with a 21 wt % solution of sodium ethoxide in ethanol (3.53 mL, 9.46 mmol). This reaction mixture was heated at 78° C. for 1 h, producing a black oil. Subsequently, the reaction mixture was cooled to room temperature, and then the reaction pH was adjusted to pH 1 with dropwise addition of 1M HCl(aq) causing the formation of a pale orange precipitate. The suspension was filtered yielding an orange solid as the pure 2-Ethyl-5-methyl-2H-pyrazole-3-carboxylic acid [4-(3-hydroxymethylene-2-oxo-2,3-dihydro-1H-indole-5-carbonyl)-phenyl]-amide (0.594 g, 1.42 mmol, 75%).

المصدر

DOI: 10.6084/m9.figshare.5104873.v1براءة الاختراع: US07749530B2uspto-grants-2010_07