N,N'-Dimethylethylenediamine → HCID 57411802, compound

Participants

Reaction Conditions

Reaction Steps

Copper (I) iodide (6.6 mg, 0.033 mmol) was added to a suspension of 2-phenoxymethyl-6,7-dihydro-5H-pyrazolo[1,5-a]pyrazin-4-one (40 mg, 0.16 mmol), 1-bromo-2,4-difluorobenzene (63 mg, 0.033 mmol), N,N′-dimethylethylenediamine (0.01 mL, 0.09 mmol) and K2CO3 (45 mg, 0.033 mmol) in toluene (2 mL). The reaction mixture was stirred at 120° C. for 16 hours. The mixture was filtered through a pad of diatomaceous earth which was washed with AcOEt. The filtrate was evaporated in vacuo. The crude product was purified by flash column chromatography (silica; AcOEt in DCM 0/100 to 20/80). The desired fractions were collected and the solvents evaporated in vacuo to yield 5-(2,4-difluoro-phenyl)-2-phenoxymethyl-6,7-dihydro-5H-pyrazolo[1,5-a]pyrazin-4-one (52 mg, 92% yield) as a white solid. 1H NMR (500 MHz, CDCl3) δ ppm 4.02-4.15 (m, 2H), 4.50-4.62 (m, 2H), 5.13 (s, 2H), 6.91-6.99 (m, 3H), 7.01 (d, J=8.4 Hz, 2H), 7.04 (s, 1H), 7.27-7.32 (m, 2H), 7.35 (td, J=8.7, 6.1 Hz, 1H).

Provenance & Evidence