Reaction #2439946

Reaction equation

2-Ethyl-5-methyl-2H-pyrazole-3-carboxylic acid [4-(3-hydroxymethylene-2-oxo-2,3-dihydro-1H-indole-5-carbonyl)-phenyl]-amide

N-(4-aminophenyl)morpholine

→

title compound

Yield 49.4%

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

Yield 49.4%

Solvents

THF

—

Hexanes

Conditions

Workup

1. 1
   OtherA small screw cap test tube
2. 2
   TemperatureSubsequently, the reaction mixture was cooled to room temperature
3. 3
   OtherThe solid precipitate that formed

Procedure

A small screw cap test tube was charged with 2-Ethyl-5-methyl-2H-pyrazole-3-carboxylic acid [4-(3-hydroxymethylene-2-oxo-2,3-dihydro-1H-indole-5-carbonyl)-phenyl]-amide (prepared below, 70 mg, 0.168 mmol) and THF (2 mL). To the resulting solution was added N-(4-aminophenyl)morpholine (32.9 mg, 0.184 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 49% (48 mg, 0.083 mmol) of the title compound.

Source