4-(Bromomethyl)benzonitrile → 4-((4R,5R)-2-Oxo-4-(5-(phenylethynyl)pyridin-3-yl)oxazolidin-5-yl)benzonitrile

Participants

Role	Name	HCID	Charge
Reactant	4-(Bromomethyl)benzonitrile	HCID 86996	—
Reactant	(4R,5R)-5-(3-Fluorophenyl)-4-(5-(phenylethynyl)pyridin-3-yl)oxazolidin-2-one	HCID 69081596	—
Product	4-((4R,5R)-2-Oxo-4-(5-(phenylethynyl)pyridin-3-yl)oxazolidin-5-yl)benzonitrile	HCID 69094289	—

Reaction Steps

Prepared according to the same procedure as (4R,5R)-5-(3-fluorophenyl)-4-(5-(phenylethynyl)pyridin-3-yl)oxazolidin-2-one, starting with 4-(bromomethyl)benzonitrile. 1H NMR (CDCl3, 500 MHz) δ: 8.80 (d, J=1.8 Hz, 1H), 8.44 (d, J=2.1 Hz, 1H), 7.90 (t, J=2.0 Hz, 1H), 7.75 (d, J=8.5 Hz, 2H), 7.53-7.63 (m, 2H), 7.35-7.48 (m, 5H), 5.39 (d, J=7.3 Hz, 1H), 4.77 (d, J=7.3 Hz, 1H). 13C-NMR (CDCl3, 126 MHz) δ: 158.1, 153.2, 146.8, 141.7, 136.4, 133.3, 133.2, 131.9, 129.4, 128.7, 126.4, 122.0, 121.6, 118.1, 113.6, 94.5, 85.0, 84.5, 62.4, 43.8, 15.0. Mass spec.: 365.9 (MH)+. The sample was further purified by SFC Prep HPLC (Chiralpak AS-H, 20% MeOH in CO2).

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US08691821B2
Source dataset	uspto-grants-2014_04
ORD ID	ord-434c82fb67d74a1a8ee2ab89847ae2f1
Source note	uspto-grants-2014_04