CHEMPACIFIC 38141

To a solution of 4-methoxy-2-methylpyridine 1-oxide (500g, 3.59mmoI) in acetic acid (l0mL) was added Fe (602g, 10.79mmol) at rt. The reaction mixture was stirred at 120 00 for 2h. The TLC showed reaction to be complete. The reaction mixture was cooled to rt and filtered through a celite pad. The filtrate was diluted with H20 (5OmL) and extracted with EtOAc (3x5OmL). The organic layer was washed with H20 (lOOmL), brine (lOOmL), dried (Na2SO4), filtered and concentrated under reduced pressure to afford 4-methoxy-2-methylpyridine as a brown oil. Yield: 250mg(56percent); 1H NMR (400 MHz, DMSO-d6): 8.23 (d, J= 5.6 Hz, 1H), 6.82 (5, 1H), 6.76 (d, J = 2.2Hz, 1H), 3.79 (5, 3H), 2.39 (5, 3H); MS (ESl+) for CHNOS m/z 124.23 [M+H].Methylzinc chloride in THF (2 M, 10.489 mL, 21 mmol) was added to a solution of 2-chloro-4-methoxypyridine (0.500 g, 3.48 mmol) and Pd(PPhEXAMPLE 4 Substituting To a solution of General procedure: To a round bottle flask containing 1 (2 mmol) was added methyl iodide (10 mmol; 5 equiv.) and the mixture was stirred at room temperature or refluxed overnight. The reaction was monitored by TLC. After completion, the resulting precipitate was separated by filtration and purified by recrystallization.In the first step, pure water (50 ml),

Molecular Weight:123.15
XLogP3:1.1
Hydrogen Bond Acceptor Count:2
Rotatable Bond Count:1
Exact Mass:123.068413911
Monoisotopic Mass:123.068413911
Topological Polar Surface Area:22.1
Heavy Atom Count:9
Complexity:85
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes