Sodium Bicarbonate → 3-{2-[3-Methyl-4-(2,2,2-trifluoro-ethoxy)pyridin-2-yl methanesulfinyl]-benzimidazole-1-sulfonyl}benzoic acid sodium salt

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Reaction Steps

A solution of 3-{2-[3-methyl-4-(2,2,2-trifluoro-ethoxy)-pyridin-2-ylmethanesulfinyl]-benzimidazole-1-sulfonyl}-benzoic acid 2-(3-nitro-benzenesulfonyl)ethyl ester (Intermediate 2, 900 mg, 1.17 mmol) and NaHCO3 (118 mg, 1.41 mmol, 1.2 eq.) in THF-H2O (6 mL-3 mL) was heated to 70° C. for 20 min, during which time the heterogeneous mixture became clear. Thereafter all the volatile materials were removed in vacuo, the residual gummy material was dissolved in CH2Cl2, and the mixture was filtered to remove solids. The filtrate was evaporated to dryness in vacuo, and the residual yellow foam was treated with ether-EtOAc (5:1) to precipitate a solid. This solid was collected by filtration to give 630 mg (94%) of 3-{2-[3-methyl-4-(2,2,2-trifluoro-ethoxy)pyridin-2-yl methanesulfinyl]-benzimidazole-1-sulfonyl}benzoic acid sodium salt (sodium salt of Compound 1).

Provenance & Evidence