3-Chloro-4-hydroxyphenylboronic acid

3-chIoro-4-hydroxyphenylboronic acid 83. To a stirred solution of 4-bromo-2-chlorophenol (5 g3-ChIoro-4-hydroxyphenylboronic acid (TJA01187) CA 1:1 mixture of Palladium acetate (26.2 mg, 0.116 mmol) and 1, 1?-Bis(di-t- butylphosphino)ferrocene (55.3 mg, 0.116 mmol) was added to a solution of Palladium acetate (0.135 g, 0.600 mmol) was added to a solution of (0.484 g, 2.81 mmol) and potassium phosphate tribasic (1.19 g, 5.62 mmol) were added to a solution of the crude tert-butyl (3 S)-3-((6-bromo-3-methyl- 1 -(tetrahydro-2H-pyran-2-yl)- 1 H-indazol-4- yl)oxy)pyrrolidine-1-carboxylate in 2:1 dioxane/water (9.5 mL), and the reaction mixturewas degassed with nitrogen for 10 minutes. (2-Dicyclohexylphosphino-2?, 4?, 6?- triisopropyl- 1, 1 ?-biphenyl)[2-(2?-amino- 1, 1 ?-biphenyl)jpalladium(II) methanesulfonate, XPhos-G3-Palladacycle (95 mg, 0.112 mmol) was added and the reaction mixture was stirred at 110 C for 3 hours under microwave irradiation. Water was added and the mixture was extracted with ethyl acetate. The ethyl acetate extracts were combined andconcentrated in vacuo to yield the crude intermediate tert-butyl (3S)-3-((6-(3-chloro-4- hydroxyphenyl)-3 -methyl-i -(tetrahydro-2H-pyran-2-yl)- 1H-indazol-4-yl)oxy)pyrrolidine- 1-carboxylate.In a pressure tube were mixed 4-{8-amino-5-chloroimidazo[1 , 2-a]pyrazi n-6-yl}benzonitrile (145 mg, 0.54 mmol), General procedure: In a pressure tube were mixed 5-phenyl-6-chloropyrazin-2-amine (100 mg, 0.49 mmol), (3- chloro-4-hydroxyphenyl)-boronic acid (100 mg, 0.58 mmol, 1.2 equiv.) and Na2003 (103 mg, 0.97 mmol, 2 equiv.) in a 4:1 mixture of 1 , 4-dioxane:water (2.5 mL). The reaction mixture wassparged with argon for 10 mm. Conditions A or B described below were then applied. The reaction mixture was then cooled down to r.t., filtered through Celite® and rinsed with EtOAc. The organic solution was washed with water and brine and aqueous layer was extracted with EtOAc. Separated organic layer was dried over anhydrous sodium sulfate, filtered and concentrated under reduced pressure to afford the crude material as a brown residue. The obtained crude mate-rial was purified by flash chromatography on silica eluting with hexane and ethyl acetate to lead to the title product as an off-white solid (40percent yield [Conditions A], 74percent yield [Conditions B]). ESl-MS: 298.15 [M+H]+. 1H NMR (400 MHz, DMSO-d6) 6 10.35 (s, 1H), 7.89 (s, 1H), 7.33 (d, J = 2.1 Hz, 1 H), 7.30 ' 7.20 (m, 5H), 6.98 (dd, J = 8.4, 2.2 Hz, 1 H), 6.79 (d, J = 8.4 Hz, 1 H), 6.59 (brs, 2H).Conditions A: Pd(PPh3)4 (8 molpercent) was then added and the reaction mixture was heated at100°C overnight.Conditions B: Pd(dppf)C12.DCM (10 molpercent) was then added and the reaction mixture was heated at 150°C for 2h.In a pressure tube were mixed 5-phenyl-6-chloropyrazin-2-amine (100 mg, 0.49 mmol), (3- chloro-4-hydroxyphenyl)-boronic acid (100 mg, 0.58 mmol, 1.2 equiv.) and Na2003 (103 mg, 0.97 mmol, 2 equiv.) in a 4:1 mixture of 1 , 4-dioxane:water (2.5 mL). The reaction mixture wassparged with argon for 10 mm. Conditions A or B described below were then applied. The reaction mixture was then cooled down to r.t., filtered through Celite® and rinsed with EtOAc. The organic solution was washed with water and brine and aqueous layer was extracted with EtOAc. Separated organic layer was dried over anhydrous sodium sulfate, filtered and concentrated under reduced pressure to afford the crude material as a brown residue. The obtained crude mate-rial was purified by flash chromatography on silica eluting with hexane and ethyl acetate to lead to the title product as an off-white solid (40percent yield [Conditions A], 74percent yield [Conditions B]). ESl-MS: 298.15 [M+H]+. 1H NMR (400 MHz, DMSO-d6) 6 10.35 (s, 1H), 7.89 (s, 1H), 7.33 (d, J = 2.1 Hz, 1 H), 7.30 ' 7.20 (m, 5H), 6.98 (dd, J = 8.4, 2.2 Hz, 1 H), 6.79 (d, J = 8.4 Hz, 1 H), 6.59 (brs, 2H).Conditions A: Pd(PPh3)4 (8 molpercent) was then added and the reaction mixture was heated at100°C overnight.Conditions B: Pd(dppf)C12.DCM (10 molpercent) was then added and the reaction mixture was heated at 150°C for 2h.

suzuki reaction

Molecular Weight:172.37
Hydrogen Bond Donor Count:3
Hydrogen Bond Acceptor Count:3
Rotatable Bond Count:1
Exact Mass:172.0098519
Monoisotopic Mass:172.0098519
Topological Polar Surface Area:60.7
Heavy Atom Count:11
Complexity:133
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes