Reaction #2439936

Reaction equation

2-Ethyl-5-methyl-2H-pyrazole-3-carboxylic acid [3-(3-hydroxymethylene-2-oxo-2,3-dihydro-1H-indole-5-carbonyl)-phenyl]-amide

N-(4-aminophenyl)morpholine

→

title compound

2-Ethyl-5-methyl-2H-pyrazole-3-carboxylic acid (3-{3-[(4-morpholin-4-yl-phenylamino)-methylene]-2-oxo-2,3-dihydro-1H-indole-5-carbonyl}-phenyl)-amide

Solvents

THF

Conditions

Workup

1. 1
   OtherA small screw cap test tube
2. 2
   TemperatureSubsequently, the reaction mixture was cooled to room temperature
3. 3
   Concentrationconcentrated in vacuo
4. 4
   workup.DISSOLUTIONredissolved in EtOAc
5. 5
   workup.ADDITIONHexanes were added to the reaction mixture
6. 6
   OtherThe solid precipitate that formed
7. 7
   Filtrationwas filtered

Procedure

A small screw cap test tube was charged with 2-Ethyl-5-methyl-2H-pyrazole-3-carboxylic acid [3-(3-hydroxymethylene-2-oxo-2,3-dihydro-1H-indole-5-carbonyl)-phenyl]-amide (prepared below, 30 mg, 0.072 mmol) and THF (1 mL). To the resulting solution was added N-(4-aminophenyl)morpholine (19.3 mg, 0.1082 mmol), and the mixture was stirred for 24 h at 65° C. Subsequently, the reaction mixture was cooled to room temperature, concentrated in vacuo and redissolved in EtOAc. Hexanes were added to the reaction mixture. The solid precipitate that formed was filtered and washed with ˜1 mL of ice cold THF yielding 36% (15 mg, 0.026 mmol) of the title compound.

Source