4-AMINO-5-BROMO-2-CHLOROPYRIDINE

A solution of 5-bromo-2~choropyridin-4-amine (5 g, 24.10 mmol) and benzoyl isothiocyanate (9.51 ml, 72.3 mmol) in acetone (25 mL) was stirred at room temperature for 18 hours. The solid was concentrated to -10 mL, filtered, washed with n-heptane and dried to give the desired product (6 g, 68 %). 1H-NMR (400 MHz, DMSO-d6) delta 13.21 (s, 1 H), 12.14 (s, 1 H), 8.76 (s, 1 H), 8.71 (s, 1 H), 7.99 (d, 2H), 7.69 (t, 1 H), 7.56 (t, 2H).MS (ESI); m/z = NA2-chloro-5-phenylpyridin-4-amineTo a mixture of 5~bromo-2- chloropyridin-4 -amine (0.2 g, 0.964 mmol) and phenylboronic acid (0.141 g, 1.157 mmol) was added dioxane (3 mL). The reaction was stirred at rt until the mixture became homogeneous, and then PdC12(dppf)-methylene chloride adduct (0.039 g, 0.048 mmol) was added. The flask was degassed and flushed with nitrogen and then aqueous sodium carbonate, (2 M, 1.446 mL, 2.89 mmol) was added dropwise, The flask was degassed and sealed and then heated at 100 C for 2 h. Saturated ammonium chloride and ethyl acetate was added. The organic layer was separated, washed with water and brine and dried over sodium sulfate. The crude product was purified by flash column chromatography using silica gel, eluting with 0-15% dichloromethane/methanol, to give the desired product (0.17 g, 0.831 mmol, 86 % yield). MS (ESI) (m/z): 205.1(M+H)+.A stirred mixture of

Molecular Weight:207.45
XLogP3:1.8
Hydrogen Bond Donor Count:1
Hydrogen Bond Acceptor Count:2
Exact Mass:205.92464
Monoisotopic Mass:205.92464
Topological Polar Surface Area:38.9
Heavy Atom Count:9
Complexity:101
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes