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

Participants

Reaction Conditions

Reaction Steps

A mixture of 7 (130 mg, 0.30 mmol) and 10% aq. sodium hydroxide (2.8 mL) in EtOH (5.8 mL) were heated at 90° C. for 1 h. The solution was cooled, partitioned between CH2Cl2/brine, the layers separated and the aqueous phase extracted with more CH2Cl2 (3×). The combined organic extracts were dried (MgSO4), concentrated and the residue purified by preparative LCMS (column LUNA 10 μ C18(2) 00G-4253-V0 250×50 mm) using water—acetonitrile (0.1% AcOH) as eluent (in gradient; flow 80 mL/min) to give 8 as a white solid (52 mg, 59%); 1H NMR (400 MHz, CDCl3+6 drops CD3OD) δ 7.13 (m, 3H), 7.22 (m, 2H), 7.47 (s, 1H), 7.80 (s, 2H), 8.27 (d, J=2.0 Hz, 1H), 8.38 (d, J=2.0 Hz, 1H).

Provenance & Evidence