1082674-24-5, 6-Bromoisoquinoline-1-carbonitrile is a isoquinoline compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated
Into a 2L 3-neck round bottom flask equipped with a mechanical stirrer, reflux condenser and thermocouple with heating mantle was placed 2-methyltetrahydrofuran (2-MeTHF) (10 mL/g; 8.15 moles; 817 mL; 702 g) followed by racemic-2,2′- bis(diphenylphosphino)-1 , 1 ‘-binaphthyl (BINAP) (0.04 equiv (molar); 14.0 mmol; 8.74 g) and bis(dibenzylideneacetone)palladium (Pd2(dba)3) (0.04 equiv (molar); 14.0 mmol; 8.07 g). The mixture was degassed by pulling vacuum and refilling with nitrogen three times then heated to 75 C for 15 minutes and cooled to ambient temperature. In a separate flask, (S)-3-amino-2-methylpropan-1 -ol (1.60 equiv; 561 mmol; 50.0 g, prepared using literature methods for example as disclosed in EP-A-0,089,139 published on 21 st September 1983) was dissolved in 2-methyltetrahydrofuran (5 mL/g; 4.08 moles; 409 mL; 351 g) and degassed by pulling vacuum and refilling with nitrogen three times. Into the pot containing the catalyst was added 6-(bromoisoquinoline-1 – carbonitrile) (1.00 equiv; 351 mmol; 81.75 g) and cesium carbonate (1.6 equiv (molar); 561 mmol; 185 g) in single portions followed by the solution of the aminoalcohol via addition funnel. The reaction mixture was again degassed by pulling vacuum and refilling with nitrogen three times. The reaction was heated to 70 C for 3 hours. The reaction was cooled to ambient temperature and filtered through a pad of Celite. The contents of the flask were rinsed out with three 100 mL portions of 2- methyltetrahydrofuran. The filtrate was transferred into a 2L round bottom flask equipped with a thermocouple and mechanical stirrer under nitrogen. Silica Gel (Silicylate SiliaMet Thiol) (0.4 g/g-pure-LR; 544 mmol; 32.7 g) was charged and the flask was stirred at 40 C overnight. The following morning, the reaction was cooled to < 30 C and filtered again through Celite. The pad was washed with 100mL of 2- methyltetrahydrofuran (or until no yellow color persisted in the filtrate). The filtrate was placed into a 3L round bottom flask equipped with a magnetic stir bar, distillation head (with condenser and receiving flask), and thermocouple. The mixture was heated to 60 C and placed under vacuum (-450-500 mbar) to distil out 1.3 L total of 2- methyltetrahydrofuran. 500 mL of toluene was added to precipitate the desired product. The heating mantle was removed and the reaction was allowed to reach ambient temperature. The mixture was stirred for 1 hour at ambient temperature and then the solids were collected by vacuum filtration on a sintered glass funnel. The cake was dried overnight on the funnel under vacuum. The following morning, the solids were transferred into an amber bottle and weighed (71.9 g; 298 mmol). The product was used in the next step without further purification., 1082674-24-5
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Reference£º
Patent; PFIZER INC.; CHEKLER, Eugene Lvovich Piatnitski; GILBERT, Adam Matthew; UNWALLA, Rayomand Jal; VERHOEST, Patrick Robert; ANDERSON, James Thomas; WO2015/181676; (2015); A1;,
Isoquinoline – Wikipedia
Isoquinoline | C9H7N – PubChem