2,6-Dibromo-4-methoxypyridine

To a solution of compound S1 (2 g, 7.11 mmol) in THF (15 mL) was added MeONa/MeOH solution (1.2 mL, 6.05 mmol, 1.3 M). The reaction was stirred at room temperature for 2 hrs and quenched with water. The resulting mixture was extracted with EtOAc twice. The combined organic phases were washed with brine, dried over anhydrous Na2, 6-Dibromo-4-methoxy pyridine (6) was obtained in 80percent yield when 2, 4, 6-tribromopyridine (5) was allowed to react with sodium methoxide (1.2 eq) in refluxing methanol. The compound (6) was treated using n-butyl lithium (1.2 eq.), was allowed to react with pivalonitrile (1.2 eq.) for 150 minutes at -78°C and was refluxed for two hours in two normal sulfuric acid to yield ketone isomer (7) in 86percent yield. An optically active alcohol (8) was obtained in 93percent yield and in 90percent ee optical purity from compound (7) through hydrogen transfer type asymmetric reduction of formic acid (4.3 eq.) and triethylamine (2.5 eq.) using the asymmetric ruthenium catalyst (RuCl[(S, S]-Tsdpen)(p-cumene), 0.01 eq.) as the catalyst. The compound (8) was converted to a camphor ester using the acid chloride, an optical resolution process was conducted using re-crystallization (75percent yield, diastereomer ratio = >99/<1) and saponified again to obtain an almost optically pure alcohol (7, quant.). The compound (7) was subjected to homo coupling using a palladium catalyst [PdCl

Molecular Weight:266.92
XLogP3:2.9
Hydrogen Bond Acceptor Count:2
Rotatable Bond Count:1
Exact Mass:266.87174
Monoisotopic Mass:264.87379
Topological Polar Surface Area:22.1
Heavy Atom Count:10
Complexity:102
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes