Acetic Acid → 2-(6-(Pyrrolidin-1-ylmethyl)thiazolo[5,4-b]pyridin-2-yl)aniline

Participants

Reaction Steps

Iron powder (55 mmol, 3.1 g) was added to a solution of 2-(2-nitrophenyl)-6-(pyrrolidin-1-ylmethyl)thiazolo[5,4-b]pyridine (11.1 mmol, 3.8 g) in CH2Cl2 (100 mL) followed by acetic acid (10 mL). The reaction mixture was heated at reflux for 3 hours then cooled to room temperature. Na2CO3 (14 g) was added in portions. The mixture was passed through a pad of celite and rinsed with CH2Cl2. The combined filtrates were washed with Na2CO3 (3×20 mL), dried (MgSO4) and concentrated under reduced pressure to give 2-(6-(pyrrolidin-1-ylmethyl)thiazolo[5,4-b]pyridin-2-yl)aniline (3.4 g, 98% yield) as a yellow solid.

Provenance & Evidence