Methyl 1-[2-(4-tert-butoxyphenoxy)ethyl]-4-(3-ethoxyphenyl)-1H-pyrrolo[3,2-c]pyridine-2-carboxylate → Methyl 4-(3-ethoxyphenyl)-1-[2-(4-hydroxyphenoxy)ethyl]-1H-pyrrolo[3,2-c]pyridine-2-carboxylate

Participants

Reaction Steps

Methyl 1-[2-(4-tert-butoxyphenoxy)ethyl]-4-(3-ethoxyphenyl)-1H-pyrrolo[3,2-c]pyridine-2-carboxylate (900 mg, 1.842 mmole) was taken up in TFA (10 mL) at RT. After 3 hr the mixture was concentrated. The residue was taken up in saturated NaHCO3 and extracted with EtOAc (3 x). The combined organic layers were dried (MgSO4), filtered, and concentrated. Flash column chromatography (Biotage-SNAP-25 g SiO2, 50% EtOAc/hexanes) gave the title compound (637 mg, 80%) as an off-white solid. 1H NMR (400 MHz, CDCl3): δ 8.49 (d, J=6.0 Hz, 1 H); 7.60 (s, 1 H); 7.52-7.38 (m, 4 H); 7.01 (dd, J=8.2, 2.5 Hz, 1 H); 6.68-6.60 (m, 3 H); 5.72 (s, 1 H); 4.97-4.91 (m, 2 H); 4.33-4.27 (m, 2 H); 4.12 (dd, J=13.9, 7.0 Hz, 2 H); 3.93 (s, 3 H); 1.43 (t, J=7.0 Hz, 3 H).

Provenance & Evidence