Formic Acid → 4-{3-[1-(2,6-Dichloro-3-fluorophenyl)ethyl]-1H-pyrrolo[2,3-b]pyridin-5-yl}-3,6-dihydro-2H-pyridine-1-carbaldehyde

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Reaction Steps

A mixture of 3-[1-(2,6-dichloro-3-fluorophenyl)ethyl]-5-(1,2,3,6-tetrahydropyridin-4-yl)-1H-pyrrolo[2,3-b]pyridine (12.0 mg, 0.0307 mmol), formic acid (2.3 μL, 0.0615 mmol), TBTU (19.7 mg, 0.0615 mmol), DIPEA (26.8 μL, 0.154 mmol) and DCM (1 mL) was stirred at rt for 30 min. The solution was concentrated in vacuo, redissolved in MeOH (0.5 mL) and purified via HPLC. The fractions containing the pure product were concentrated in vacuo to afford the title compound as a white solid. 1H NMR (400 MHz, CD3OD): δ=1.87 (d, J=7.3 Hz, 3 H), 2.36-2.58 (m, 2H), 3.63-3.80 (m, 2 H), 4.05-4.15 (m, 2 H), 5.26 (q, J=7.2 Hz, 1 H), 5.86-5.97 (m, 1 H), 7.18 (t, J=8.7 Hz, 1 H), 7.24-7.31 (m, 1 H), 7.32-7.54 (m, 2 H), 8.09-8.17 (m, 1 H), 8.22 (d, J=2.0 Hz, 1 H). MS (ES+): m/z 418.04 (100) [MH+]. HPLC: tR=3.40 min (ZQ3, polar—5 min).

Provenance & Evidence