Reaction #2439957

Reaction equation

N-[4-(3-Hydroxymethylene-2-oxo-2,3-dihydro-1H-indole-5-carbonyl)-phenyl]-acetamide

4-(4-methyl-piperazin-1-yl)-phenylamine

→

title compound

Yield 62.6%

N-[4-(3-{[4-(4-Methyl-piperazin-1-yl)-phenylamino]-methylene}-2-oxo-2,3-dihydro-1H-indole-5-carbonyl)-phenyl]-acetamide

Yield 62.6%

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 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 4-(4-methyl-piperazin-1-yl)-phenylamine (32.6 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 62% (48 mg, 0.097 mmol) of the title compound.

Source