2-Bromo-3-chloro-5-hydroxypyridine

Preparation of R2 group [0259] 5-chloro-6-(l-hydroxyethyl)pyridin-3-ol: Step 1. To a solution of 5-C1- 6-Bromopyridine-3-o 1(1.1 g, 5.28 mmol) in DMF (10 mL) was added 2- ethoxyvinyltributyltin ( 2.86 g, 7.93 mmol) and PdCl2(PPh3)2 (185 mg, 0.26 mmol). The mixture was heated at 110 C for 5 h. The mixture was concentrated under vacuum and dissolved in acetone (10 mL). 2N HCl (3 mL) was added. The mixture was then stirred at room temp for 3 h. The mixture was concentrated, neutralized to PH 7 and extracted with ethyl acetate. The organic layer was dried and concentrated to give black oil which was chromatographed on silica gel to give the methyl ketone as a pale yellow solid (1.0 g). [0260] Step 2. To a solution of ketone (1.0 g, 5.84 mmol) in methanol ( 10 ml) was added NaB (666 mg, 17.5 mmol). The mixture was heated at 50 C for 30 min. After this period, the mixture was concentrated and partitioned between ethyl acetate and water. The water layer was neutralized with 2N HCl and extracted with ethyl acetate. The organic layers were dried and concentrated. Silica gel chromatography of the residue gave the title compound as a pale red solid (470 mg, 48%). 1H-NMR (400 MHz) delta 8.12 (d, 1H), 7.23 (d, 2H), 5.20 (brs, 1H), 5.09 (m, 1H), 4.16 (d, 1H), 1.45 (d, 3H).

Molecular Weight:208.44
XLogP3:2.1
Hydrogen Bond Donor Count:1
Hydrogen Bond Acceptor Count:2
Exact Mass:206.90865
Monoisotopic Mass:206.90865
Topological Polar Surface Area:33.1
Heavy Atom Count:9
Complexity:103
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes