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

Participants

Reaction Conditions

Reaction Steps

To a suspension of 60% sodium hydride in mineral oil (503 mg, 12.6 mmol) in DMF (10 mL) cooled to 0° C. is added a solution of diethyl 1H-pyrrolo[2,3-b]pyridine-2,6-dicarboxylate (Intermediate D, 3.00 g, 11.4 mmol) in DMF (10 mL), dropwise. The mixture is stirred at 0° C. for 30 min after which a solution of tert-butyl (5S)-5-methyl-1,2,3-oxathiazolidine-3-carboxylate 2,2-dioxide (2.71 g, 11.4 mmol) in DMF (10 mL) is added. The mixture is allowed to warm and stir at room temperature for 16 h. The reaction is quenched with H2O and is 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 0-30% ethyl acetate/heptane to afford the title compound (3.00 g, 63%). LCMS: 442.86 (M+Na+).

Provenance & Evidence