2-(4-BROMO-1H-PYRAZOL-1-YL)PYRIMIDINE

To a solution of General procedure: The ligand pzpm (47.4mg, 0.32mmol) was dissolved in CH2Cl2 (10ml), and added to a suspension of [NiBr2(DME)] (100mg, 0.32mmol) in CH2Cl2 (20ml), in a Schlenk tube, under nitrogen. The reaction was stirred for 18h at room temperature. The resulting suspension was filtered and the solid product was washed twice with hexane (2×10ml) and dried in vacuum, yielding 94mg (82%) of a mustard yellow powder.To a solution of propane- 1 -sulfonic acid {3-[ l-(2, 6-dichloro-benzoyl)-5-(4, 4, 5, 5-tetramethyl- [l , 3, 2]dioxaborolan-2-yl)- 1 H-pyrrolo[2, 3-b]pyridine-3-carbonyl]-2, 4-difluoro-phenyl}-amide (32, 18 mg, 0.026 mmol) and 2-(4-bromo-pyrazol-l -yl)-pyrimidine (33, 4.95 mg, 0.022 mmol) in 800 muL· of acetonitrile is added 400 mu of 1 aqueous potassium carbonate and approximately 1-2 mg of [Iota , Gamma- bis(diphenylphosphino)ferrocene] dichloro-palladium (II) (PdCI2 dppf). The reaction mixture is microwave irradiated at 145 C for 15 minutes, then neutralized with acetic acid, and extracted with 2 x 1 mL of ethyl acetate. The combined organic layer is concentrated under vacuum, the residue dissolved in 500 x of dimethylsulfoxide and purified by HPLC using a CI 8 column, eluting with water/acetonitrile and 0.1 % trifluoroacetic acid, 20-100% acetonitrile at 6 mL per minute. Appropriate fractions are combined and concentrated under vacuum to provide the desired compound. MS (ESI) [M+H+]+ = 524.5.To a solution of 2-pyrazol-1-yl-pyrimidine (0.55 g, 3.7 mmol) in acetic acid (5 ml_) was added bromine (1.2 g, 7.5 mmol) in acetic acid (3 ml_) dropwisely. After addition, the reaction mixture was stirred at room temperature overnight. After removed the acetic acid, the crude product was purified using column chromatography (2% methanol in dichloromethane) to give 0.7 g of pure product in 85 % yield. MS (ESMS, M+H 225).To a solution of 2-pyrazol-1-yl-pyrimidine (0.55 g, 3.7 mmol) in acetic acid (5 ml_) was added bromine (1.2 g, 7.5 mmol) in acetic acid (3 mL) dropwisely. After addition, the reaction mixture was stirred at room temperature overnight. After removed the acetic acid, the crude product was purified using column chromatography (2% methanol in dichloromethane) to give 0.7 g of pure product in 85 % yield.A solution containing A solution containing

Molecular Weight:225.05
XLogP3:1.2
Hydrogen Bond Acceptor Count:3
Rotatable Bond Count:1
Exact Mass:223.96976
Monoisotopic Mass:223.96976
Topological Polar Surface Area:43.6
Heavy Atom Count:12
Complexity:148
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes