SYNTHESIS OF 5-FLUORO-2-OXINDOLE DERIVATIVES THROUGH KNOEVENAGEL REACTION

• Main Author: Florencia Tanuwidjaja, Aurielle
• Format: Final Project
• Language: Indonesia
• Subjects: Kimia
• Online Access: https://digilib.itb.ac.id/gdl/view/82758
• Institution: Institut Teknologi Bandung

Sunitinib is an anticancer drug that has been approved in multiple countries for the therapy of gastrointestinal stromal tumor (GIST) and renal cell carcinoma (RCC), however patients have shown various symptoms of toxicity. Therefore this research aims to synthesize derivatives of 5-fluoro-2-oxindole through the Knoevenagel condensation reaction with piperidine as the basic catalyst. This study has successfully synthesized 6 new compunds that have not previously been reported, 5-fluoro-3-(2,3-dimethoxybenzyl)indolin-2-on (2) with a yield of 73%%; 5-fluoro-3-(2,3,4-trimethoxybenzyl)indolin-2-on (4) with a yield of 66,7%; 5-fluoro-3-(2-nitrobenzyl)indolin-2-on (7) with a yield of 42,2%; 5-fluoro-3-(4 hydroxybenzyl)indolin-2-on (10) with a yield of 83,6%; 5-fluoro-3-(4 (diethylamino)benzyl)indolin-2-on (12) with a yield of 58,8%; and 5-fluoro-3-(3-ethoxy-4 hydroxybenzyl)indolin-2-on (14) with a yield of 57,2%. This study has also successfully synthesized 10 other compunds that have previosuly been reported, 5-fluoro-3 benzylindolin-2-on (1) with a yield of 45,1%; 5-fluoro-3-(2,4-dimethoxybenzyl)indolin-2 on (3) with a yield of 71,9%; 5-fluoro-3-(2,4,5-trimethoxybenzyl)indolin-2-on (5) with a yield of 87,2%; 5-fluoro-3-(3,4,5-trimethoxybenzyl)indolin-2-on (6) with a yield of 83,7%; 5-fluoro-3-(4-nitrobenzyl)indolin-2-on (8) with a yield of 84,5%; 5-fluoro-3-(4 methoxybenzyl)indolin-2-on (9) with a yield of 47,3%; 5-fluoro-3-(4 methylbenzyl)indolin-2-on (11) with a yield of 69,6%; 5-fluoro-3-(3,4 dimethoxybenzyl)indolin-2-on (13) with a yield of 78,9%; 5-fluoro-3-(4 (dimethylamino)benzyl)indolin-2-on (15) with a yield of 37,7%; and ethyl 5-((5-fluoro-2 oxoindolin-3-ylidene)methyl)-2,4-dimethyl-1H-pyrrole-3-carboxylate (16) with a yield of 91,6%. Each synthesized product has been charaterized using 1H-NMR, 13C-NMR and MS. Based on the results, synthesized 5-fluoro-2-oxindole derivatives have shown the appropriate data.