Reaktion #577186

Reaktionsgleichung

4′-Trifluoromethyl-2-biphenylcarboxylic acid

oxalyl chloride

pyridine

product

3-chloro-1N-methyl-5-amino-indole-2-carboxylic acid ethyl ester

→

title compound

3-chloro-1-methyl-5-[(4′-trifluoromethyl-biphenyl-2-carbonyl)-amino]-1H-indole-2-carboxylic acid ethyl ester

Lösungsmittel

DMF

methylene chloride

CH2Cl2

methylene chloride

Reaktionsbedingungen

Aufarbeitung

1. 1
   Waschenwashed with 0.1 N HCl solution (2×500 mL) and with brine (500 mL)
2. 2
   Trocknendried (MgSO4)
3. 3
   SonstigeThe solvent was evaporated in vacuo
4. 4
   Sonstigeto give the crude product which
5. 5
   Sonstigewas purified by recrystallization from EtOAc/isooctane

Vorschrift

4′-Trifluoromethyl-2-biphenylcarboxylic acid was converted to the corresponding acid chloride by treatment with oxalyl chloride in methylene chloride in the presence of catalytic amount of DMF. To a solution of the acid chloride (10.8 g, 38 mmol) and pyridine (3.27 mL, 40 mmol) in methylene chloride (200 mL) was added the product of step (c) (10.1 g, 40 mmol), and the reaction mixture was stirred at room temperature for 1 hour. The reaction solution was diluted to 600 mL with CH2Cl2, washed with 0.1 N HCl solution (2×500 mL) and with brine (500 mL), and then dried (MgSO4). The solvent was evaporated in vacuo to give the crude product which was purified by recrystallization from EtOAc/isooctane to afford 13.8 g of the title compound.

Quelle