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

Participants

Role	Name	HCID	Charge
Reactant	Phenylacetylene	HCID 10821	—
Reactant	(+)-(4R,5R)-5-(3-Methoxyphenyl)-4-(3-(phenylethynyl)phenyl)oxazolidin-2-one	HCID 69083418	—
Reactant	(4R,5R)-4-(5-Bromopyridin-3-yl)-5-(3-fluorophenyl)oxazolidin-2-one	HCID 69084164	—
Product	(4R,5R)-5-(3-Fluorophenyl)-4-(5-(phenylethynyl)pyridin-3-yl)oxazolidin-2-one	HCID 69081596	—

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-bromopyridin-3-yl)-5-(3-fluorophenyl)oxazolidin-2-one and phenylacetylene. 1H-NMR (CDCl3, 500 MHz) δ 8.78 (bs, 1H), 8.42 (bs, 1H), 7.90 (m, 1H), 7.57 (m, 2H), 7.35-7.45 (m, 4H), 7.02-7.17 (m, 3H), 6.83 (bs, 1H), 5.30 (d, J=7.3, 1H), 4.83 (d, J=7.3, 1H). 13C-NMR (CDCl3, 126 MHz) δ 164.2, 162.2, 158.6, 152.9, 146.9, 139.1 (d, J=7.7), 136.4, 133.7 (br), 131.9, 131.1 (d, J=8.6), 129.3, 128.7, 122.1, 121.6 (d, J=2.9), 116.6 (d, J=21), 113.0 (d, J=23), 94.2, 85.2, 84.9, 62.5. Mass spec.: 359.3 (MH)+.

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US08691821B2
Source dataset	uspto-grants-2014_04
ORD ID	ord-e1112a1c23ff4c8bb520e9e9a861acc4
Source note	uspto-grants-2014_04