Methanol → HCID 58557399, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of 8-iodo-6-((2-(trimethylsilyl)ethoxy)methyl)-6H-pyrrolo[2,3-e][1,2,4]triazolo[4,3-a]pyrazine (0.050 g, 0.12 mmol, prepared using KK from Preparation #GGG.1.1 and NaH), TEA (0.034 mL, 0.24 mmol), MeOH (0.25 mL, 6.2 mmol), and DMF (0.6 mL) purged with nitrogen was added [1,1′-bis(diphenylphosphino)ferrocene]dichloropalladium(II) (0.0098 g, 0.012 mmol). The mixture was purged with CO and a balloon of CO was attached to the reaction vessel. The mixture was warmed to about 100° C. After about 4.5 h, the solution was allowed to cool to ambient temperature. Water (5 mL) was added and the mixture was extracted with EtOAc (2×10 mL). The combined organics were dried over anhydrous Na2SO4, filtered, and concentrated under reduced pressure. The crude material was purified by silica gel chromatography eluting with a gradient of 25-75% EtOAc/heptane over 30 min to afford methyl 6-((2-(trimethylsilyl)ethoxy)methyl)-6H-pyrrolo[2,3-e][1,2,4]triazolo[4,3-a]pyrazine-8-carboxylate (0.0311 g, 74%): LC/MS (Table 1, Method n) Rt=0.74 min; MS m/z: 348 (M+H)+.

Provenance & Evidence