Triethylamine → HCID 89649640, compound

Participants

Reaction Conditions

Reaction Steps

To a stirred solution of phenyl vinyl sulfone (7307.08 mg, 43.44 mmol) in methanol (80 mL) was added 3-amino-1-methyl-pyrrolidin-2-one (4958.41 mg, 43.44 mmol), 4-bromo-5-ethyl-pyridine-2-carbaldehyde (CAS: 1256833-98-3) (9300 mg, 43.44 mmol) and calcium triflate (734.57 mg, 2.17 mmol). The reaction was stirred for 10 minutes, and then the reaction was cooled to −10° C., and then triethylamine (6.04 mL, 43.44 mmol) was added dropwise. The reaction was then stirred at room temperature for 4 hours. The reaction was concentrated in vacuo, and redissolved in THF (150 mL). The reaction was cooled to 00° C., and to the reaction mixture was added potassium tert-butoxide (14622.41 mg, 130.31 mmol) portionwise. The reaction was then stirred for 2 hours while allowing to warm to room temperature. The reaction was then filtered through celite, and the celite was washed with DCM (150 mL). The filtrate was then concentrated in vacuo. The residue was purified by column chromatography over silica (340 g, Biotage SNAP cartridge), eluting with EtOAc:isohexane from 0% to 100%. Fractions containing the desired product were combined and concentrated in vacuo to give 2-(4-bromo-5-ethyl-2-pyridyl)-7-methyl-1,7-diazaspiro[4.4]non-1-en-6-one (D121) (3091 mg, 9.1931 mmol, 21.2% yield) as a brown oil approximately 85% pure and used directly in the next step;

Provenance & Evidence