Tetrahydrofuran → HCID 136348435, compound

Participants

Reaction Conditions

Reaction Steps

To THF (5 mL) was added 4-(4-bromo-2-methyl-phenyl)-1,3,6,6-tetramethyl-7,8-dihydro-4H-pyrazolo[3,4-e][1,4]thiazepine (0.1 g, 0.26 mmol, Example D.58), trans-di-MU-acetatobis[2-(di-o-tolylphosphino)benzyl]dipalladium(II) (0.025 g, 0.026 mmol, Alfa Aesar), molybdenumhexacarbonyl (0.072 g, 0.26 mmol, Fluka), tri-tert-butylphosphonium tetrafluoroboronate (0.016 g, 0.052 mmol), 1,8-diazabicyclo[5.4.0]undec-7-ene (0.061 g, 0.052 mmol) and 3-aminopyridine (0.075 g, 0.78 mmol). The resulting mixture was heated, in a sealed microwave vessel, for about 1 h at about 120° C. in a microwave. After cooling to rt, the mixture was filtered and partitioned between ethyl acetate (50 mL) and 5% aqueous sodium bicarbonate (25 mL). The layers were separated and the organic layer was washed with 5% aqueous sodium bicarbonate (10 mL), dried (MgSO4), filtered and concentrated in vacuo. The resulting oil was purified by column chromatography (SiO2, ethyl acetate followed by 2% MeOH/ethyl acetate to 5% MeOH/ethyl acetate) to afford 3-methyl-N-(3-pyridyl)-4-(1,3,6,6-tetramethyl-7,8-dihydro-4H-pyrazolo[3,4-e][1,4]thiazepin-4-yl)benzamide (0.071 g, 64%) as white solid: LC-MS (Table 1, Method e) Rt=4.87 min, m/z 422 (M+H)+

Provenance & Evidence