4-(4-Aminophenyl)butanoic acid → 4-[4-[[6-[3-[(3-methylthiophene-2-carbonyl)amino]benzoyl]-2-oxo-1H-indol-3-ylidene]methylamino]phenyl]butanoic acid

Participants

Reaction Conditions

Reaction Steps

A small screw cap test tube was charged with 3-Methyl-thiophene-2-carboxylic acid [3-(3-hydroxymethylene-2-oxo-2,3-dihydro-1H-indole-6-carbonyl)-phenyl]-amide (as prepared in Example 352, 200 mg, 0.4945 mmol) and THF (5.0 mL). To the resulting solution was added 4-(4-Amino-phenyl)-butyric acid (88.6 mg, 0.494 mmol), and the mixture was stirred for 24 h at 65° C. Subsequently, the reaction mixture was cooled to room temperature and concentrated in vacuo. The crude residue was purified by flash silica gel chromatography (CHCl3:MeOH mix eluant with gradient of 1% MeOH to 15% MeOH) to afford the title compound in 43% yield (0.120 g, 0.212 mmol).

Provenance & Evidence