5-Chloro-2-fluoropyridine

Colorless to brown liquid

By following the above procedures, and employing the appropriate starting pyridine compounds, the following compounds are prepared:2, 5-Difluoropyridine; 2, 5-dibromopyridine; 2-chloro-5-bromopyridine; 2-chloro-5-fluoropyridine; 2-fluoro-5-chloropyridine; 2-bromo-5-chloropyridine; and 2-bromo-5-fluoropyridine.Representative halopyridine compounds which can be prepared by the method of the present invention include:...2, 5-difluoropyridine; 2, 5-dibromopyridine; 2-chloro-5-bromopyridine; 2-chloro-5-fluoropyridine; 2-fluoro-5-chloropyridine; 2-fluoro-5-bromopyridine; 2-bromo-5-chloropyridine; 2-bromo-5-fluoropyridine; ...A solution of Intermediate 28 in THF was cooled to -78C and treated with tert-butyllithium (1.6M in hexane, 5 equiv.). The solution was stirred for 1 h, then the appropriate aryl halide (1.5 equiv.) in THF was added. Once the reaction was complete, the mixture was quenched with brine and extracted with EtOAc. The organic layer was washed with water and brine, then dried with sodium sulfate. The solvent was removed. The crude material was purified by preparative HPLC, then deprotected in accordance with General Method 2. As necessary, final products were further purified by preparative reverse phase HPLC (pH 3).A solution of Asolution of /V-[5-[(iTo a stirred mixture of compound 3 (3g, 16.48mmol, 1 eq) and compound 4 (4.31 g, 32.96mmol, 2eq) was added 1 M Li-HMDS (164mL, 164.83mmol, 10eq, in THF) at RT then added xantphos (571 mg, 0.989mmol, 0.06eq) and Pd2(dba)3 (452mg, 0.494mmol, 0.03eq) at RT. The reaction mixture was heated to 80C for 16h. TLC analysis indicated formation of a less polar spot. The reaction mixture was filtered through celite pad then the filtrate was concentrated to give a crude residue, which was diluted with EtOAc (100ml_) then washed with water (2x60ml_). The organic layer was dried over Na2S04 then concentrated to a crude compound. The crude compound was purified by column chromatography (silica gel, 100-200 mesh) using 0-5% EtOAc in petroleum ether as eluent to afford compound 5 (3g, %) as a color less oil. LC-MS: m/z 294.31 (M + HTo a solution of (1 R, 5S)-3-benzyl-3, 8- diazabicyclo[3.2.1]octane (6 g, 29.7 mmol, 1 .0 eq) in DMSO (60 mL) was added K2CO3 (12.3 g, 89.1 mmol, 3.0 eq) then

Molecular Weight:131.53
XLogP3:1.9
Hydrogen Bond Acceptor Count:2
Exact Mass:130.9938050
Monoisotopic Mass:130.9938050
Topological Polar Surface Area:12.9
Heavy Atom Count:8
Complexity:78.8
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes