Reacción #2439958

ord-8a593491a98645e3a57de5e48b68365c

Ecuación de reacción

CC(=O)Nc1ccc(C(=O)c2ccc3c(c2)C(=CO)C(=O)N3)cc1
N-[4-(3-Hydroxymethylene-2-oxo-2,3-dihydro-1H-indole-5-carbonyl)-phenyl]-acetamide
C1CCOC1
THF
COc1ccc(N)cc1O
5-Amino-2-methoxy-phenol
CC(=O)Nc1ccc(C(=O)c2ccc3c(c2)C(=CNc2ccc(C)c(O)c2)C(=O)N3)cc1
title compound
Rendimiento 63.0%
CC(=O)Nc1ccc(C(=O)c2ccc3c(c2)C(=CNc2ccc(C)c(O)c2)C(=O)N3)cc1
N-(4-{3-[(3-Hydroxy-4-methyl-phenylamino)-methylene]-2-oxo-2,3-dihydro-1H-indole-5-carbonyl}-phenyl)-acetamide
Rendimiento 63.0%

Disolventes

Condiciones de reacción

Temperatura
65°CELSIUS
Condiciones detalladas
See reaction.notes.procedure_details.

Tratamiento posterior

  1. 1
    OtroA small screw cap test tube
  2. 2
    TemperaturaSubsequently, the reaction mixture was cooled to room temperature
  3. 3
    OtroThe solid precipitate that formed

Procedimiento

A small screw cap test tube was charged with N-[4-(3-Hydroxymethylene-2-oxo-2,3-dihydro-1H-indole-5-carbonyl)-phenyl]-acetamide (as prepared in Example 11, 50 mg, 0.155 mmol) and THF (2 mL). To the resulting solution was added 5-Amino-2-methoxy-phenol (21.0 mg, 0.170 mmol), and the mixture was stirred for 24 h at 65° C. Subsequently, the reaction mixture was cooled to room temperature. Hexanes were added to the reaction mixture. The solid precipitate that formed was washed with ˜1 mL of i-prOH yielding 63% (42 mg, 0.098 mmol) of the title compound.

Fuente

DOI: 10.6084/m9.figshare.5104873.v1Patente: US07749530B2uspto-grants-2010_07