* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.
With caesium carbonate In methanol; water; tolueneHeating / reflux
A mixture of 2-bromopyrimidine (0.43g,2.70mmol), 2-bromopyridine-5-boronic acid (0.55g,2.72mmol), tetrakis(triphenylpnosphine)palladium(0) (3OOmg, 0.259mmol), cesium carbonate (1.15g, 3.03mmol) was stirred in MeOH/toluene/water (15ml, 1/1/1) at reflux temperature overnight. The reaction was cooled to room temperature and diluted with EtOAc (200ml) and water (50ml). The organic layer was separated, dried over MgSd, filtered and solvent evaporated yielding a residue which was purified on silica gel eluting with 25percent v/vEtOAc/hexanes yielding product 76 as white solid. (0.55g, 85percent) ESMS (MH, 236).
5%
With caesium carbonate In methanol; water; tolueneHeating / reflux
A mixture of 2-bromopyridine (0.43g,2.70mmol), 2-bromopyridine-5-boronic acid (0.55g,2.72mmol), tetrakis(triphenylphosphine)palladium(0) (3OOmg, 0.259mmol), cesium carbonate (1.15g, 3.03mmol) was stirred in MeOH/toluene/water (15ml, 1/1/1) at reflux temperature overnight. The reaction was cooled to room temperature and diluted with EtOAc (200ml) and water (50ml). The organic layer was separated, dried over MgSO4,filtered and solvent evaporated yielding a residue which was purified on silica gel eluting with 25percent v/vEtOAc/hexanes yielding product 76 as white solid. (0.55g, 5percent) ESMS (MH, 236).
With potassium carbonate; In N,N-dimethyl-formamide; at 100.0℃; for 1.0h;
A mixture of 2-(6-Bromo-pyridin-3-yl)-pyrimidine 76 (100mg, Q.425mmol), potassium carbonate (100mg,0.724mmol), and piperazine (100mg,1.16mmol) in DMF (5mi) were stirred at 1000C for 1 hour. The reaction was cooled.solvent evaporated under reduced pressure, and the residue dissolved in MeCb (150ml), washed with H2O (50ml),dried over MgSO4,filtered and evaporated solvent yielding title product 77 as a white solid (100mg,98%). ESMS (MH, 242).
98%
With potassium carbonate; In N,N-dimethyl-formamide; at 100.0℃; for 1.0h;
A mixture of 2-(6-Bromo-pyridin-3-yl)-pyrimidine 76 (100mg, 0.425mmol), potassium carbonate (100mg,0.724mmol), and piperazine (100mg,1.16mmol) in DMF' (5ml), were stirred at 1000C for 1 hour. The reaction was cooled, solvent evaporated^/ - under reduced pressure, and the residue dissolved in MeCI2 (150ml), washed with H2O (50ml),dried over MgSO4,filtered and evaporated solvent yielding title product 77 as a white solid (100mg,98%). ESMS (MH, 242).
With caesium carbonate;tetrakis(triphenylphosphine) palladium(0); In methanol; water; toluene;Heating / reflux;
A mixture of 2-bromopyrimidine (0.43g,2.70mmol), 2-bromopyridine-5-boronic acid (0.55g,2.72mmol), tetrakis(triphenylpnosphine)palladium(0) (3OOmg, 0.259mmol), cesium carbonate (1.15g, 3.03mmol) was stirred in MeOH/toluene/water (15ml, 1/1/1) at reflux temperature overnight. The reaction was cooled to room temperature and diluted with EtOAc (200ml) and water (50ml). The organic layer was separated, dried over MgSd, filtered and solvent evaporated yielding a residue which was purified on silica gel eluting with 25% v/vEtOAc/hexanes yielding product 76 as white solid. (0.55g, 85%) ESMS (MH, 236).
5%
With caesium carbonate;tetrakis(triphenylphosphine) palladium(0); In methanol; water; toluene;Heating / reflux;
A mixture of 2-bromopyridine (0.43g,2.70mmol), 2-bromopyridine-5-boronic acid (0.55g,2.72mmol), tetrakis(triphenylphosphine)palladium(0) (3OOmg, 0.259mmol), cesium carbonate (1.15g, 3.03mmol) was stirred in MeOH/toluene/water (15ml, 1/1/1) at reflux temperature overnight. The reaction was cooled to room temperature and diluted with EtOAc (200ml) and water (50ml). The organic layer was separated, dried over MgSO4,filtered and solvent evaporated yielding a residue which was purified on silica gel eluting with 25% v/vEtOAc/hexanes yielding product 76 as white solid. (0.55g, 5%) ESMS (MH, 236).
With caesium carbonate;(1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; In 1,4-dioxane; water; for 4.0h;
Refluxed mixture of 2-(6-Bromo-pyridin-3-yl)-pyrimidine (1Q) (200mg, 0.85mmol), N-tert-butoxycarbonyl-1 ,2,3,6-tetrahydropyridine-4-boronic acid, pinacol ester (290mg, 0.93mmol); Cesium Carbonate (500mg, 1.538mmol); PdCI2dppf (30mg) in dioxane/H2O (10ml v/v 4/1 ) for 4 hours. Cooled reaction, then evaporated solvent. Extracted with EtOAc (200ml) washed with H2O (50ml), dried over MgSO4, filtered and solvent evaporated yielding a solid which chromatographed on silica gel eluting with 30% v/v acetone/hexanes yielding 2Q as a white solid (110mg, 38%) ESMS (MH.339).
With N-ethyl-N,N-diisopropylamine; In N,N-dimethyl-formamide; at 80.0℃;
Example 31 To a stirred solution of 10 (3.05g, 12.9 mmol) in DMF (30 mL) 1 (5.97 mL, 38.7 mmol) and DIPEA (8.5 mL, 51.7 mmol) was added. The clear mixture was heated at 80 C overnight before concentrated to a small volume and partitioned between ethyl acetate and brine. The separated organic layer was dried and concentrated to dryness. The resulting crude was purified on silica gel column (eluting with 15% to 30% ethyl acetate in hexanes) to yield 11 as a brown solid (4.5 g, 84%).
Chemistry
Pharmaceutical Intermediates
Inhibitors/Agonists
Material Science
For Research Only
120K+ Compounds
Competitive Price
1-2 Day Shipping
