5-Bromo-2-(bromomethyl)pyridine → HCID 69086210, compound

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Reaction Steps

Prepared from (4R,5R)-4-(5-bromopyridin-2-yl)-5-(3-fluorophenyl)oxazolidin-2-one using the same procedure as that used to prepare (4R,5R)-5-(3-fluorophenyl)-4-(6-(phenylethynyl)pyridin-3-yl)oxazolidin-2-one from 5-bromo-2-(bromomethyl)pyridine. The two enantiomers were purified via chiral preparative liquid chromatography (Chiralpak AS 21×250 10 μm, A=0.1% Diethylamine/Heptane, B=Ethanol, Isocratic 45% B for 15 min, Flow Rate=15 mL/min) providing 8.5 mg (15%) (4S,5S)-5-(3-fluorophenyl)-4-(5-(phenylethynyl)pyridin-2-yl)oxazolidin-2-one and 6.2 mg (11%) (4R,5R)-5-(3-fluorophenyl)-4-(5-(phenylethynyl)pyridin-2-yl)oxazolidin-2-one. 1H NMR (500 MHz, CDCl3) δ ppm 8.79 (1H, d, J=1.53 Hz), 7.90 (1H, dd, J=8.09, 1.98 Hz), 7.51-7.62 (2H, m), 7.32-7.45 (5H, m), 7.14-7.24 (2H, m), 7.08 (1H, td, J=8.32, 1.98 Hz), 5.77 (1H, s), 5.57 (1H, d, J=5.80 Hz), 4.90 (1H, d, J=5.19 Hz). Chiral LC for (4S,5S)-5-(3-fluorophenyl)-4-(5-(phenylethynyl)pyridin-2-yl)oxazolidin-2-one; example 409 (Chiralpak OJ-H analytical column, 4.6×100 mm, 5 μm, Mobile Phase: A=100% Heptane with 0.1% Diethylamine, B=100% Ethanol, Flow rate: 2.0 mL/min, 40% A Isocratic) 4.57 min. Chiral LC for (4R,5R)-5-(3-fluorophenyl)-4-(5-(phenylethynyl)pyridin-2-yl)oxazolidin-2-one; example 410 (Chiralpak OJ-H analytical column, 4.6×100 mm, 5 μm, Mobile Phase: A=100% Heptane with 0.1% Diethylamine, B=100% Ethanol, Flow rate: 2.0 mL/min, 40% A Isocratic) 9.94 min.

Provenance & Evidence