4-CHLORO-5-FLUORO-2-PYRIDINEMETHANOL

(iv) Substituting 2-methyl-4-chloro-5-fluoropyridine-N-oxide (13 g) for 2-methyl-3-fluoro-4-chloropyridine-N-oxide and using corresponding molar proportions of the other reagents in the method of Example 27(iv), gave 2-hydroxymethyl-4-chloro-5-fluoropyridine (6.83 g) m.p. 50-52.To a solution of Intermediate 47 (200 mg) in CH2Cl2 (5 ml) was added manganese oxide (861 mg). The suspension was stirred overnight and filtered eluting with CH2Cl2. The filtrate was concentrated in vacuo to afford 130 mg (66%) of the title compound as a yellow oil. 1H-NMR (delta, ppm, CDCl3): 10.00 (s, 1 H), 8.64 (s, 1 H), 8.06 (d, 1 H).4-Chloro-5-fluoro-2-methylpyridine 1-oxide (840 mg) (for a synthesis see J. Med. Chem., 1989, 32, 1970-1977) was refluxed in Ac2O (6 ml) for 1 h. After adding H2O, the pH was adjusted to 9 with aqueous 2N NaOH. The aqueous phase was extracted with CH2Cl2, dried over Na2SO4, filtered and concentrated under vacuum to give 700 mg of a mixture of the (4-chloro-5-fluoro-2-pyridinyl)methyl acetate (majority) and 4-Chloro-5-fluoro-2-methylpyridine 1-oxide (840 mg) (for a synthesis see J. Med. Chem., 1989, 32, 1970-1977) was refluxed in Ac2O (6 ml) for 1 h. After adding H2O, the pH was adjusted to 9 with aqueous 2N NaOH. The aqueous phase was extracted with CH2Cl2, dried over Na2SO4, filtered and concentrated under vacuum to give 700 mg of a mixture of the (4-chloro-5-fluoro-2-pyridinyl)methyl acetate (majority) and A mixture of 6'-[3-(dimethylamino)-1-pyrrolidinyl]-4-hydroxy-2/-/-1 , 3'-bipyridin-2-one (150 mg, 0.499 mmol) and triphenylphosphine (327 mg, 1.249 mmol) was treated with (v) Substituting

Molecular Weight:161.56
XLogP3:0.7
Hydrogen Bond Donor Count:1
Hydrogen Bond Acceptor Count:3
Rotatable Bond Count:1
Exact Mass:161.0043696
Monoisotopic Mass:161.0043696
Topological Polar Surface Area:33.1
Heavy Atom Count:10
Complexity:114
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes