5-(Bromomethyl)-2-chloropyridine → HCID 86673453, compound

HRID 2362435Notes

Reaction equation

HRID 2362435 reaction equation
Br[CH2:2][C:3]1[CH:4]=[CH:5][C:6]([Cl:9])=[N:7][CH:8]=1.BrC1C=C([C@@H]2[C@@H:21]([C:22]3[CH:27]=[C:26]([F:28])[CH:25]=[CH:24][C:23]=3F)[O:20][C:19](=[O:30])[NH:18]2)C=NC=1.BrC1C=NC=C(CBr)C=1>>[Cl:9][C:6]1[N:7]=[CH:8][C:3]([C@@H:2]2[C@@H:21]([C:22]3[CH:23]=[CH:24][CH:25]=[C:26]([F:28])[CH:27]=3)[O:20][C:19](=[O:30])[NH:18]2)=[CH:4][CH:5]=1

Participants

4

Reactant 3

HCID 64246615-(Bromomethyl)-2-chloropyridineHCID 149329483-Bromo-5-(bromomethyl)pyridineHCID 69083834HCID 69083834, compound

Product 1

HCID 86673453HCID 86673453, compound

Procedure

Prepared from 5-(bromomethyl)-2-chloropyridine in similar fashion to the preparation of (4R,5R)-4-(5-bromopyridin-3-yl)-5-(2,5-difluorophenyl)oxazolidin-2-one from 3-bromo-5-(bromomethyl)pyridine. 1H NMR (500 MHz, CDCl3) δ ppm 8.19-8.36 (1H, m), 7.72 (1H, dd, J=8.39, 2.59 Hz), 7.42-7.49 (1H, m), 7.32-7.42 (1H, m), 6.94-7.08 (2H, m), 5.56 (1H, s), 5.23 (1H, d, J=7.63 Hz), 4.77 (1H, d, J=7.63 Hz). Mass Spectral Anal. Calcd. for [M+H]+ C14H10ClFN2O2: 293.0. found 293.1.

Sources & evidence

ORD record
ord-bab498258fa9447e85e56d44b0d04c4e
Source dataset
uspto-grants-2014_04
Patent number
US08691821B2

Reaction notes

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