Diethylene Glycol Monomethyl Ether → HCID 131727235, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of methyl 3-(chloromethyl)-1-(2,4-difluorobenzyl)-1H-pyrrolo[2,3-c]pyridine-5-carboxylate (4 mL, 0.197M in CH2Cl2, 0.788 mmol)) [prepared as described in step 2 of example 40] in anhydrous DMF (10 mL) was added 2-(methoxyethoxy)-ethanol (0.47 g, 3.94 mmol, 0.43 mL, 5 eq.) followed by i-Pr2NEt (0.407 g, 3.14 mmol, 0.55 mL, 4 eq.). The mixture, under nitrogen, was placed in an oil bath and the bath was warmed to 40° C. After stirring for 24 hours (40° C.) the reaction was judged to by complete by HPLC-MS analysis and the volatiles were removed in vacuo (ca. 2 torr) to give a golden yellow oil. The crude material was purified by chromatography on a column of silica gel (40 mm OD, 100 g, 230-400 mesh, packed and eluted with CH2Cl2-EtOAc 70:30 v/v, 0.4 L, CH2Cl2-EtOAc-MeOH 80:18:2 1.0 L, and CH2Cl2-EtOAc-MeOH 80:17.5:2.5 1.0 L, 25 mL fractions) using the flash technique. Fractions 42-80 were combined to afford 0.339 g (78%) of methyl 1-(2,4-difluorobenzyl)-3-{[2-(2-methoxyethoxy)ethoxy]methyl}-1H-pyrrolo[2,3-c]pyridine-5-carboxylate: 2-(methoxyethoxy)-ethanol (1:1) as a clear, colorless, viscous oil.

Provenance & Evidence