3-Amino-4-fluorophenylboronic acid, pinacol ester

2-Fluoro-5-(4, 4, 5, 5-tetramethyl-l, 3, 2-dioxaborolan-2-yl)aniline (14)[00198] A 500-mL Parr reactor bottle was purged with nitrogen and charged with 13 (6.92 g, 25.9 mmol), ethyl acetate (150 mL) and 10percent palladium on carbon (50percent wet, 150 mg dry weight). The bottle was attached to Parr hydrogenator, evacuated, charged with hydrogen gas to a pressure of 50 psi and shaken for 2 h. After this time the hydrogen was evacuated and nitrogen charged into the reactor. The catalyst was removed by filtration through a pad of Celite 521 and the filter cake washed with methylene chloride (400 mL). The resulting solution was concentrated under reduced pressure to afford 14 in 100percent yield (6.34 g) as a yellow oil: A vial was charged with 5-bromo-2-fluoroaniline (1 g, 5.26 mmol), bis(pinacolato)diboron (1.6 g , 6.31 mmol), potassium acetate (1.03 g, 10.52 mmol), Pd(dppf)ClUnder an argon atmosphere, 4.2 mg (0.015 mmol) of dichlorobis (trimethylphosphine) nickel, 72.8 mg (0.5 mmol) of 5-chloro-2-fluoroaniline, 152 mg (1.0 mmol) of cesium fluoride, 140 mg (0.55 mmol) of 4, 4, 5, 5, 4 ', 4', 5 ', 5'-octamethyl-2, 2'-bi (1, 3, 2-dioxaborolanyl)180 mg (1.05 mmol) of trimethyl (2, 2, 2-trifluoroethoxy) silane and 0.5 mL of tetrahydrofuran were added and sealed, And the mixture was stirred at 100 ° C. for 12 hours.After the reaction vessel was cooled to room temperature, 1 mL of a saturated aqueous solution of ammonium chloride was added, and the mixture was extracted three times with 8 mL of ethyl acetate, and the obtained organic phases were combined.The solvent was distilled off under reduced pressure, and the residue was purified using silica gel column chromatography (hexane: chloroform: ethyl acetate = 4: 1: 0 to 4: 1: 1)96 mg (pale yellow liquid, yield 81percent) of 2-fluoro-5- (4, 4, 5, 5-tetramethyl-1, 3, 2-dioxaborolan-2-yl) aniline was obtained

Molecular Weight:237.08
Hydrogen Bond Donor Count:1
Hydrogen Bond Acceptor Count:4
Rotatable Bond Count:1
Exact Mass:237.1336371
Monoisotopic Mass:237.1336371
Topological Polar Surface Area:44.5
Heavy Atom Count:17
Complexity:282
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes