Sodium hydride → Diethyl 1-{3-[(tert-butoxycarbonyl)amino]butan-2-yl}-1H-pyrrolo[2,3-b]pyridine-2,6-dicarboxylate

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To a solution of diethyl 1H-pyrrolo[2,3-b]pyridine-2,6-dicarboxylate (Intermediate D, 3.40 g, 13.0 mmol) in DMF (15 mL) cooled to 0° C. is added 60% sodium hydride in mineral oil (570 mg, 14.3 mmol). The mixture is stirred at 0° C. for 20 min after which a solution of tert-butyl 4,5-dimethyl-1,2,3-oxathiazolidine-3-carboxylate 2,2-dioxide (5.35 g, 14.3 mmol) in DMF (10 mL) is added. The mixture is stirred at 0° C. for 30 min after which the reaction was allowed to warm and stir at ambient temperature overnight. The reaction is quenched with H2O and was stirred for 15 min. The mixture is extracted with ethyl acetate and the combined organic phases are washed with brine, and are dried (Na2SO4). The solvent is removed in vacuo and the crude material is purified via flash column chromatography using a gradient elution of 0-20% ethyl acetate/heptane to afford the title compound as a colorless oil (6.00 g, quantitative). LCMS: 434.83 (M+H+).

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