Sodium Hydroxide → 5-(2,3-dihydro-benzofuran-5-yl)-3-(1H-pyrazol-4-yl)-1H-pyrrolo[2,3-b]pyridine

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Reaction Conditions

Reaction Steps

To 49 (45 mg, 0.10 mmol) in EtOH (3 mL) was added 10% aq. NaOH (1.25 mL) and the reaction mixture was heated at 85° C. for 1 h. The mixture was concentrated to afford a yellow solid. Purification by preparative LCMS (column LUNA 10μ C18(2) 00G-4253-V0 250×50 mm) using water—acetonitrile (0.1% AcOH) as eluent (in gradient; flow 80 mL/min) afforded the product 50 (16 mg, 53%) as a white solid; 1H NMR (400 MHz, CD3OD) δ 3.24 (t, J=17.4, 8.7 Hz, 2H), 4.55 (t, J=17.4, 8.7 Hz, 2H), 6.80 (d, J=8.2 Hz, 1H), 7.36 (d, J=8.2 Hz, 1H), 7.50 (s, 1H), 7.58 (s, 1H), 7.98 (s, 2H), 8.24 (s, 1H), 8.38 (s, 1H).

Provenance & Evidence