Diisopropylethylamine → HCID 5279908, compound

Participants

Reaction Steps

To a solution of (7-chloro-1H-pyrrolo[3,2-b]pyridin-3-yl)-oxo-acetic acid (1.5 g, 6.7 mmol) and phenylpiperidine-4-ylidene acetonitrile (1.3 g, 6.7 mmol) in DMF (50 mL) was added DEPBT (3.15 g, 10.5 mmol) and ethyl diisopropylamine (6.1 mL, 35 mmol). The solution was stirred 20 h, concentrated under vacuum and partitioned between 5% Na2CO3(aq) (80 mL) and EtOAc (5×100 mL). The combine organic layers were dried (MgSO4), filtered and concentrated. The residue was purified by Biotage Chromatography (SiO2, 30% EtOAc/Hex to 100% EtOAc) and by preparative HPLC to yield the title compound (300 mg, 0.74 mmol, 11%) as a yellow solid.

Provenance & Evidence