Cesium carbonate → HCID 69146057, compound

Temperature

120 °C

315 mg (2.5 mmol) of N-allylpiperazine were dissolved in 5 ml of toluene under an argon atmosphere. 93 mg (0.1 mmol) of tris-(dibenzylideneacetone)-dipalladium(0) (Pd2 dba3), 126 mg (0.2 mmol) of 2,2′-bis-(diphenylphosphino)-1,1′-binaphthyl (BINAP), 1.14 g (3.5 mmol) of cesium carbonate and 515 mg (2.54 mmol) of 5-bromo-2-nitropyridine were then added and the mixture was stirred at 120° C., in a microwave oven, for 4 hours. After the reaction mixture had cooled down to room temperature, a saturated aqueous solution of ammonium chloride was added. After that, the aqueous reaction mixture was extracted three times with in each case 50 ml of ethyl acetate. After the organic phase had been dried over sodium sulfate, the drying agent had been filtered off and the solvent had been evaporated down to dryness, the residue was chromatographed through silica gel using ethyl acetate/methanol (4:1), with 304 mg (46% of theory) of the title compound being obtained.

1. temperatureAfter the reaction mixture had cooled down to room temperature
2. extractionAfter that, the aqueous reaction mixture was extracted three times with in each case 50 ml of ethyl acetate
3. dry with materialAfter the organic phase had been dried over sodium sulfate
4. filtrationthe drying agent had been filtered off
5. customthe solvent had been evaporated down to dryness
6. customthe residue was chromatographed through silica gel

ORD record

ord-ec471ef36d7f4c5d83d9dedad4aef415

Source dataset

uspto-grants-2013_07

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08476275B2