Pyridine → (6-(1-((3,4-Difluorobenzyl)-methyl-amino)-ethylideneamino)-2-hydroxyindan-1-yl)-carbamic acid tert-butyl ester

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Reaction Steps

Add methyl trifluoromethanesulfonate (0.750 g, 3.49 mmol) to a solution of N-(3,4-difluorobenzyl)-N-methylthioacetamide (0.145 g, 0.736 mmol) in 10 mL of CH2Cl2 at room temperature. Stir the mixture for 30 minutes and remove the solvent under reduced pressure. Then add (6-amino-2-hydroxyindan-1-yl)-carbamic acid t-butyl ester (0.78 g, 2.97 mmol) followed by 5 mL of pyridine. The resulting mixture is stirred for 12 h. After pyridine is evaporated, the residue is purified by column chromatograph (silica gel, 3% MeOH in CH2Cl2) to give 0.98 g of (6-(1-((3,4-difluorobenzyl)-methyl-amino)-ethylideneamino)-2-hydroxyindan-1-yl)-carbamic acid tert-butyl ester as a white solid: MS 446 (MH+).

Provenance & Evidence