Cesium fluoride → HCID 53386257, compound

Participants

Reaction Conditions

Reaction Steps

In a round-bottomed flask, 2-cyclopropyl-5-(2-trimethylsilanyl-ethoxymethyl)-5H-pyrrolo[2,3-b]pyrazine-7-carboxylic acid [(R)-1-(4-hydroxy-4-phenyl-piperidine-1-carbonyl)-2,2-dimethyl-propyl]-amide (0.21 g, 0.33 mmol) was dissolved in acetonitrile (4.2 mL). 18-Crown-6 (89 mg, 0.33 mmol) and cesium fluoride (507 mg, 3.34 mmol) were added. The reaction mixture was stirred at 85° C. overnight and then at room temperature for 24 h. Silica Gel (˜1 g) was added to the reaction mixture and the suspension was concentrated and purified by chromatography over 12 g SiO2 with 0-100% EtOAc/heptane to 0-10% MeOH/EtOAc to afford an oil. Trituration with dichloromethane/hexanes afforded 45 mg (26%) of 2-cyclopropyl-5H-pyrrolo[2,3-b]pyrazine-7-carboxylic acid [(R)-1-(4-hydroxy-4-phenyl-piperidine-1-carbonyl)-2,2-dimethyl-propyl]-amide as a yellow powder. MS: (M+H)+=476.

Provenance & Evidence