2-Methoxy-5-pyridineboronic acid

White to beige powder

Intermediate 25a : [6-(methyloxy)-3-pyridinyl]boronic acidTo a stirred solution of 17.0 ml_ (0.131 mol) of 5-bromo- 2methoxypyridine in 130 ml_ THF at -78Step i: 6-Methoxypyridin-3-ylboronic acid (R-3-1) (0154) To a solution of compound 303 (20 g, 0.11 mole) in anhydrous THF (180 ml) was added dropwise n-BuLi (59 mL, 2M in THF) at −78° C., the resulting mixture was stirred for 1 h. Triisopropyl borate (37 mL) was added at −78° C. and the reaction mixture was warmed to room temperature and continued to stir overnight. TLC (hexanes/ethyl acetate=5:1) showed reaction complete. The mixture was adjusted pH to 3-4 with 4N HCl (90 ml). The precipitate was collected by filtration to afford crude compound R-3-1 (21 g, 128percent). The crude compound R-3-1 (21 g) was dissolved in water (200 ml) and the solution was adjusted pH to 8-9 with concentrated ammonia solution, the precipitate was collected by filtration to afford the pure title compound R-3-1 as a white solid. (11 g, 67percent). LCMS (m/z): 154.1 [M+1]To a solution of compound 303 (20 g, 0.11 mole) in anhydrous THF (180 ml) was added dropwise n-BuLi (59 mL, 2M in THF) at -78 °C, the resulting mixture was stirredfor 1 h. Triisopropyl borate (37mL) was added at -78 °C and the reaction mixture was warmed to room temperature and continued to stir overnight. TLC (hexanes/ethyl acetate =5:1) showed reaction complete. The mixture was adjusted pH to 3-4 with 4N HC1 (90 ml). The precipitate was collected by filtration to afford cmde compound R-3-1 (21 g, 128percent). The cmde compound R-3-1 (21g) was dissolved in water (200 ml) and the solutionwas adjusted pH to 8-9 with concentrated ammonia solution, the precipitate was collected by filtration to afford the pure title compound R-3-1 as a white solid. (11 g, 67percent). LCMS (m/z): 154.1 [M+1f ‘HNMR(400MF{z, DMSO-d6): ö3.86(s, 3H), 6.76 (d, J= 8.4 Hz, 1H), 7.99 (dd, J= 8.4 Hz, 2.0 Hz, 1H), 8.05 (br, 2H), 8.52 (d, J 2.0 Hz, 1H).6-Methoxy-3-pyridylboronic acid

Molecular Weight:152.95
Hydrogen Bond Donor Count:2
Hydrogen Bond Acceptor Count:4
Rotatable Bond Count:2
Exact Mass:153.0597233
Monoisotopic Mass:153.0597233
Topological Polar Surface Area:62.6
Heavy Atom Count:11
Complexity:122
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes