2-(4-(1,3-Dioxan-2-yl)-2-fluorophenyl)-5-(1-(4-(benzyloxy)phenyl)cyclopropyl)thiazolo[5,4-b]pyridine → 4-(5-(1-(4-(Benzyloxy)phenyl)cyclopropyl)thiazolo[5,4-b]pyridine-2-yl)-3-fluorobenzaldehyde

Participants

Reaction Conditions

Reaction Steps

A suspension of 2-(4-(1,3-dioxan-2-yl)-2-fluorophenyl)-5-(1-(4-(benzyloxy)-phenyl)cyclopropyl)thiazolo[5,4-b]pyridine (0.305 g, 0.566 mmol) in 5 mL THF and 5 mL 5N aq. HCl was heated in a sealed vial to 65° C. for 1 h. The reaction mixture was cooled, poured onto ice, quenched with 10 N NaOH, sonicated in 5 mL MTBE, filtered, and rinsed with 1 mL MTBE. The solid was collected to give 4-(5-(1-(4-(benzyloxy)-phenyl)cyclopropyl)thiazolo[5,4-b]pyridine-2-yl)-3-fluorobenzaldehyde as an orange solid. MS (ESI) m/z: calculated: 480.1; Observed: 481.1 (M++1).

Provenance & Evidence