Water → 4,5-Difluoro-3-(2-fluoro-4-iodophenyl)-1H-benzofuro[6,7-d]imidazol-2(3H)-one

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Reaction Steps

For scale up synthesis, CDI(92.4 g, 570 mmol) was added to a solution of 4,5-difluoro-N6-(2-fluoro-4-iodo-phenyl)-benzofuran-6,7-diamine (153.6 g, 380.1 mmol) in 1500 mL of DCM at 0° C. The solution was then warmed to room temperature and stirred for approximately 48 hours. Analysis showed 0.3% remaining of 4,5-difluoro-N6-(2-fluoro-4-iodo-phenyl)-benzofuran-6,7-diamine with 86.1% purity. The solution was filtered to give crude gray solid with 96.4% purity. The crude was dissolved in 1.5 L of THF and then water (1.5 L) was added. The suspension was then concentrated to 1.7 L and filtered to give 87 g of product with 98.0% purity (53.2% yield). 1H NMR (DMSO-d6, 400 MHz): δ 12.29 (bs, 1H), 8.09 (d, 1H), 7.94 (dd, 1H), 7.76 (d, 1H), 7.47 (t, 1H), 7.19 (d, 1H).

Provenance & Evidence