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

HRID 2362468Notes

Reaction equation

HRID 2362468 reaction equation
Br[C:2]1[CH:3]=[CH:4][C:5]([C@@H:8]2[C@@H:12]([C:13]3[CH:18]=[CH:17][CH:16]=[C:15]([F:19])[CH:14]=3)[O:11][C:10](=[O:20])[NH:9]2)=[N:6][CH:7]=1.F[C:22]1[CH:23]=[C:24]([C@H:28]2OC(=O)N[C@@H:29]2C2C=NC(C#CC3C=CC=CC=3)=CC=2)[CH:25]=[CH:26][CH:27]=1.BrC1C=CC(CBr)=NC=1>>[F:19][C:15]1[CH:14]=[C:13]([C@@H:12]2[O:11][C:10](=[O:20])[NH:9][C@H:8]2[C:5]2[CH:4]=[CH:3][C:2]([C:29]#[C:28][C:24]3[CH:25]=[CH:26][CH:27]=[CH:22][CH:23]=3)=[CH:7][N:6]=2)[CH:18]=[CH:17][CH:16]=1.[F:19][C:15]1[CH:14]=[C:13]([C@H:12]2[O:11][C:10](=[O:20])[NH:9][C@@H:8]2[C:5]2[CH:4]=[CH:3][C:2]([C:29]#[C:28][C:24]3[CH:25]=[CH:26][CH:27]=[CH:22][CH:23]=3)=[CH:7][N:6]=2)[CH:18]=[CH:17][CH:16]=1

Participants

5

Reactant 3

HCID 234380625-Bromo-2-(bromomethyl)pyridineHCID 69083905HCID 69083905, compoundHCID 69085234HCID 69085234, compound

Product 2

HCID 69083145HCID 69083145, compoundYield 11%HCID 69086210HCID 69086210, compoundYield 15%

Procedure

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.

Workup

  1. customThe two enantiomers were purified via chiral preparative liquid chromatography (Chiralpak AS 21×250 10 μm

Sources & evidence

ORD record
ord-846f7382f7934bd49713ff6dc47372a3
Source dataset
uspto-grants-2014_04
Patent number
US08691821B2

Reaction notes

Loading…