2-Methylthio-1-pyrroline → N-(3,4-dihydro-2H-pyrrol-5-yl)-4-methyl-1-(phenylsulfonyl)-1H-pyrrolo[2,3-b]pyridin-5-amine

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Reaction Steps

A solution of 4-methyl-1-(phenylsulfonyl)-1H-pyrrolo[2,3-b]pyridin-5-amine, (775 mg, 2.7 mmol) and 5-(methylthio)-3,4-dihydro-2H-pyrrole (345 mg) in i-PrOH (14 mL) was heated at 105° C. for 3 days. The refluxed mixture was then cooled to room temperature and concentrated. Flash column chromatography (4-6% 7N NH3 in MeOH/DCM) yielded N-(3,4-dihydro-2H-pyrrol-5-yl)-4-methyl-1-(phenylsulfonyl)-1H-pyrrolo[2,3-b]pyridin-5-amine, (180 mg) 1H NMR (300 MHZ, CD3OD) δ: 8.10 (d, J=7.6 Hz, 2H), 7.89 (s, 1H), 7.75 (d, J=4.1 Hz, 1H), 7.63 (s, 1H), 7.54 (d, J=8.2 Hz, 2H), 6.77 (d, J=4.1 Hz, 1H), 2.63 (s, 2H), 2.09 (t, J=7.5 Hz, 3H).

Provenance & Evidence