2-Chloro-5-fluoro-3-pyridinecarboxaldehyde

2-chloro-5-fluoro-pyridine-3-carbaldehyde (1.00 g, 6 · 27 mmol) was added to a 20 ml microwave vial, 2-benzyl-4, 4, 5, 5-tetramethyl-1, 3, 2-dioxaborolane (1.1 equivalents, 6.89 mmol) [1, 1'-bis (diphenylphosphino) ferrocene] palladium (II) dichloride (PdCl2 (dppf); 0 ' 1 equivalent, 0.63 mmol ) And powdered sodium carbonate (3 equiv., 18.8 mmol). Add 1, 4-dioxane (9 mL) and water (5 mL) The mixture was rinsed with nitrogen and then passed through a microwave 90 C under heating for two 2 hours. The cooled mixture was then directly adsorbed onto silica and purified by trituration on a 40 g silica gel column eluting with isohexane: ethyl acetate (100%: 0% to 70%: 30%) to afford the title compound as a colorless oil 2-benzyl-5-fluoro-pyridine-3-carbaldehyde (460 mg). (20 g, 125 mmol) was taken up in THF (150 ml) at 0 C. (R)-2-Methylpropane-2-sulfinamide (16.71 g, 138 mmol) was added followed by dropwise additionof titaniumtetraethanolate (22.88 ml, 150 mmol). The reaction mixture was stirred while warming to RT. After 3 hours the reaction mixture was cooled to 0 C, and 150m1 of brine was added and stirred for 20 minutes. The mixture was filtered through Celite. The aqueous layer was separated and discarded. The organic layer with dried over Na2SO4 and the solvent was removed to give(S , Z)-N-((2-chloro-5-fluoropyridin-3 -yl)methylene)-2-methylpropane-2- sulfinamide (32 g, 122 mmol, 97 % yield), which was carried on without further purification. LCMS: 263 M+H.To a stirred solution of methyl 2-sulfanylbenzoate (2.5 g, 14.86 mmol) in DMF (30 ml)were added Cs2CO3 (7.267 g, 22.29 mmol) followed by (20 g, 125 mmol) was taken up in THF (150 ml) at 0 C. (R)-2-Methylpropane-2-sulfinamide (16.71 g, 138 mmol) was added followed by dropvvise addition of iitaniumtetraethanolaie (22.88 ml, 150 mmol). The reaction mixture was stirred while warming to RT. After 3 hours the reaction mixture was cooled to 0 C, and 150ml of brine was added and stirred for 20 minutes. The mixture was filtered through Celite. The aqueous layer was separated and discarded. The organic layer with dried over Na2S04 and the solvent was removed to give (S, Z)-N-((2-chloro-5-fluoropyridm-3-yl)memylene)-2-methylpropane-2-sul.finaiTiide (32 g, 122 mmol, 97 % yield), which was carried on without further purification. LCMS: 263 M+H.

Molecular Weight:159.54
XLogP3:1.4
Hydrogen Bond Acceptor Count:3
Rotatable Bond Count:1
Exact Mass:158.9887196
Monoisotopic Mass:158.9887196
Topological Polar Surface Area:30
Heavy Atom Count:10
Complexity:133
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes