Hexane → 2,3-Dimethyl-6-mehylthiopyrrolo[2,3-b]pyridine

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Reaction Steps

A deaerated solution of 6-bromo-2,3-dimethyl-pyrrolo [2,3-b]pyridine (225 mg, 1.0 mmol) in 25 ml dry THF was cooled to -78° C. and treated with 1.6M n-BuLi in hexane (1,5 ml, 2.4 mmol). The reaction mixture was brought to 0° C. and the lithiate trapped with dimethyl disulfide (444 μl, 5 mmol). After reacting for 5 min 1.5 ml H2O was added and the THF evaporated. The residue was taken up in 100 ml CH2Cl2 and washed with 50 ml 5% NaHCO3, 50 ml 2M HCl (reextracted twice with 25 ml CH2Cl2), and 50 ml 5% NaHCO3. The organic layer was dried over MgSO4 and evaporated leaving 160 mg (83%) pure 2,3-dimethyl-6-methylthio-pyrrolo[2,3-b]pyridine.

Provenance & Evidence