3-Ethoxy-5-fluorophenylboronic acid

A solution of DBU (20 mu, , 0.133 mmol) and Intermediate El (60 mg, 0.129 mmol) in acetonitrile (4 mL) was added to a vial charged with CuTMEDA (10 mg, 0.022 mmol) and A vial containing a mixture of N-((6-aminopyridin-2-yl)sulfonyl)-6-chloro-2-(mesityloxy)-nicotinamide (30. mg, 0.067 mmol), 3-ethoxy-5-fluoro-benzeneboronic acid (25 mg, 0.13 mmol), Pd(PPh3)4 (5.0 mg), K3PO4 (2.0 M, 0.13 mL) and N, N-dimethylformamide (0.6 mL) was flushed with nitrogen and sealed. The mixture was then heated at 80 C. overnight before it was cooled and diluted with DMSO (0.3 mL). The mixture was subjected to preparatory-HPLC (30-90% acetonitrile/water with 5 muM HCl) to give N-[(6-amino-2-pyridyl)sulfonyl]-6-(3-ethoxy-5-fluoro-phenyl)-2-(2, 4, 6-trimethylphenoxy)pyridine-3-carboxamide (Compound 1255) (20 mg, 54%). ESI-MS m/z calc. 550.2. found 551.5 (M+1)+. Retention time: 3.15 min (5 min run).SM011-Ethoxy-3-fluoro-5-iodobenzene(3-Ethoxy-5-fluorophenyl)boronic acid (2.5 g, 0.014 mol) was dissolved in THF (30 mL) and a solution of sodium iodide (4.1 g, 0.028 mol) in H20 (15 mL) was added followed by a solution of chloramine T (7.8 g, 0.1 mol) in H20 (15 mL). After 20 h stirring , the reaction mixture was extracted with diethylether (3x 50 mL). The organic layers were combined and the solvent was evaporated. The resulting residue was triturated with hexanes (3x) and the hexanes layers were combined. The solvent was evaporated to yield 1 -Ethoxy-3-fluoro-5-iodobenzene as an orange oil. The product was used in the next reaction step without further purification.

suzuki reaction

Molecular Weight:183.97
Hydrogen Bond Donor Count:2
Hydrogen Bond Acceptor Count:4
Rotatable Bond Count:3
Exact Mass:184.0707025
Monoisotopic Mass:184.0707025
Topological Polar Surface Area:49.7
Heavy Atom Count:13
Complexity:156
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes