3-CYANOPYRIDIN-4-YLBORONIC ACID

Under a nitrogen atmosphere, 300 g of anhydrous tetrahydrofuran was added to the reaction flask, stirring was continued, 12 g of 3-cyano-pyridine was added and cooled to -30C.N-BuLi was slowly added dropwise to 70 mL of 2.0 M, and after stirring for 30 minutes, a solution of 1, 4, 7, 10-tetramethyl-1, 4, 7, 10-tetraazacyclododecane was slowly added dropwise.After 2 hours of incubation, 41 mL of triisopropyl borate was slowly added dropwise at -30 ° C, stirred for 1 hr, slowly raised to room temperature and stirred for 1 hour.And 400 g of concentrated hydrochloric acid was added thereto, followed by stirring for 1 hour to carry out a hydrolysis reaction.The layers were allowed to stand, and the organic layer was washed three times with water (3 x 100 g).The aqueous layers were combined and the aqueous layer was extracted once with 100 ml of petroleum ether. The combined organic layers were dried over 50 g of anhydrous sodium sulfate and filtered.The filtrate was concentrated to dryness to give 3-cyano-4-pyridine boronic acid 14 g, Under a nitrogen atmosphere, 300 g of anhydrous tetrahydrofuran was added to the reaction flask, stirring was continued, 12 g of 3-cyano-pyridine was added and cooled to -30C.N-BuLi was slowly added dropwise to 70 mL of 2.0 M, and after stirring for 30 minutes, 26 g of 1, 4, 7-trimethyl-1, 4, 7-triazacyclononane was slowly added dropwise.After incubation for 2 hours, 26 mL of trimethyl borate was slowly added dropwise at -30 ° C, stirred for 1 hr, slowly warmed to room temperature and stirred for 1 hour.And 400 g of concentrated hydrochloric acid was added thereto, followed by stirring for 1 hour to carry out a hydrolysis reaction.The layers were allowed to stand, and the organic layer was washed three times with water (3 x 100 g).The aqueous layers were combined and the aqueous layer was extracted once with 100 ml of petroleum ether. The combined organic layers were dried over 50 g of anhydrous sodium sulfate and filtered.The filtrate was concentrated to dryness to give 13 g of 3-cyano-4-pyridine boronic acid.Under a nitrogen atmosphere, 300 g of anhydrous tetrahydrofuran was added to the reaction flask, stirring was continued, 12 g of 3-cyano-pyridine was added and cooled to -30C.N-BuLi was slowly added dropwise to 70 mL of 2.0 M, and after stirring for 30 minutes, 26 g of 1, 4, 7-trimethyl-1, 4, 7-triazacyclononane was slowly added dropwise.After incubation for 2 hours, 26 mL of trimethyl borate was slowly added dropwise at -30 C, stirred for 1 hr, slowly warmed to room temperature and stirred for 1 hour.And 400 g of concentrated hydrochloric acid was added thereto, followed by stirring for 1 hour to carry out a hydrolysis reaction.The layers were allowed to stand, and the organic layer was washed three times with water (3 x 100 g).The aqueous layers were combined and the aqueous layer was extracted once with 100 ml of petroleum ether. The combined organic layers were dried over 50 g of anhydrous sodium sulfate and filtered.The filtrate was concentrated to dryness to give 13 g of 3-cyano-4-pyridine boronic acid.Under a nitrogen atmosphere, 300 g of anhydrous tetrahydrofuran was added to the reaction flask, stirring was continued, 12 g of 3-cyano-pyridine was added and cooled to -30C.N-BuLi was slowly added dropwise to 70 mL of 2.0 M, and after stirring for 30 minutes, a solution of 1, 4, 7, 10-tetramethyl-1, 4, 7, 10-tetraazacyclododecane was slowly added dropwise.After 2 hours of incubation, 41 mL of triisopropyl borate was slowly added dropwise at -30 C, stirred for 1 hr, slowly raised to room temperature and stirred for 1 hour.And 400 g of concentrated hydrochloric acid was added thereto, followed by stirring for 1 hour to carry out a hydrolysis reaction.The layers were allowed to stand, and the organic layer was washed three times with water (3 x 100 g).The aqueous layers were combined and the aqueous layer was extracted once with 100 ml of petroleum ether. The combined organic layers were dried over 50 g of anhydrous sodium sulfate and filtered.The filtrate was concentrated to dryness to give 3-cyano-4-pyridine boronic acid 14 g,

Molecular Weight:147.93
Hydrogen Bond Donor Count:2
Hydrogen Bond Acceptor Count:4
Rotatable Bond Count:1
Exact Mass:148.0444076
Monoisotopic Mass:148.0444076
Topological Polar Surface Area:77.1
Heavy Atom Count:11
Complexity:177
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes