Phenylacetylene → (4R,5R)-5-(2,5-Difluorophenyl)-4-(2-fluoro-5-(phenylethynyl)pyridin-3-yl)oxazolidin-2-one

Participants

Role	Name	HCID	Charge
Reactant	Phenylacetylene	HCID 10821	—
Reactant	(4R,5R)-4-(5-Bromo-2-fluoropyridin-3-yl)-5-(2,5-difluorophenyl)oxazolidin-2-one	HCID 69082811	—
Reactant	(+)-(4R,5R)-5-(3-Methoxyphenyl)-4-(3-(phenylethynyl)phenyl)oxazolidin-2-one	HCID 69083418	—
Product	(4R,5R)-5-(2,5-Difluorophenyl)-4-(2-fluoro-5-(phenylethynyl)pyridin-3-yl)oxazolidin-2-one	HCID 69082915	—

Reaction Steps

Prepared according to the same procedure as (+)-(4R,5R)-5-(3-methoxyphenyl)-4-(3-(phenylethynyl)phenyl)oxazolidin-2-one, starting with (4R,5R)-4-(5-bromo-2-fluoropyridin-3-yl)-5-(2,5-difluorophenyl)oxazolidin-2-one and phenylacetylene. 1H NMR (CDCl3) δ: 8.37 (d, J=1.2 Hz, 1H), 8.11 (dd, J=8.9, 2.1 Hz, 1H), 7.56 (dd, J=7.6, 1.8 Hz, 2H), 7.35-7.42 (m, 3H), 7.21-7.26 (m, 1H), 7.07-7.14 (m, 2H), 6.99 (s, 1H), 5.57 (d, J=5.8 Hz, 1H), 5.07 (d, J=5.8 Hz, 1H). 19F NMR (CDCl3) δ: −71.32 (br. s., 1F), −117.12 (br. s., 1F), −123.54 (d, J=8.7 Hz, 1F). Mass spec.: 395.1 (MH)+.

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US08691821B2
Source dataset	uspto-grants-2014_04
ORD ID	ord-6e97981742e742dfbacc31256f9606d5
Source note	uspto-grants-2014_04