Methyl iodide → 5-(1,3-Dioxolan-2-yl)-1-methyl-1H-pyrrolo[2,3-c]pyridine

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Reaction Steps

5-(1,3-Dioxolan-2-yl)-1H-pyrrolo[2,3-c]pyridine (C173) (1.05 g, 5.52 mmol) is dissolved in 20 mL THF in a dried flask under N2. 60% Sodium hydride (243 mg, 6.07 mmol) is added, the reaction is stirred 30 min, methyl iodide (360 μL, 5.8 mmol) is added, and the reaction is stirred overnight at rt. The reaction is concentrated in vacuo and the residue is partitioned between 10 mL saturated NaCl and CH2Cl2 (4×10 mL). The combined organic layer is dried over anhydrous K2CO3 and is concentrated in vacuo to a tan paste. The crude material is chromatographed over 50 g silica gel (230-400 mesh) eluting with 5% MeOH/CH2Cl2. The appropriate fractions are combined and concentrated to afford 5-(1,3-dioxolan-2-yl)-1-methyl-1H-pyrrolo[2,3-c]pyridine (C175) (86% yield). HRMS (FAB) calculated for C11H12N2O2+H: 205.0977, found 205.0983.

Provenance & Evidence