Sodium Carbonate → 1-(1-Hydroxypropan-2-yl)-5-(thiophen-2-yl)pyridin-2(1H)-one

Participants

Role	Name	HCID	Charge
Reactant	Sodium Carbonate	HCID 10340	—
Reactant	2-Thiopheneboronic acid	HCID 2733960	—
Reactant	5-Bromo-1-(1-hydroxypropan-2-yl)pyridin-2(1H)-one	HCID 58070342	—
Catalyst	Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)	HCID 178418228	—
Solvent	Water	HCID 962	—
Solvent	Ethyl Acetate	HCID 8857	—
Solvent	1,4-Dioxane	HCID 31275	—
Product	1-(1-Hydroxypropan-2-yl)-5-(thiophen-2-yl)pyridin-2(1H)-one	HCID 59843066	29%

Reaction Conditions

Temperature	90 °C

Reaction Steps

To a solution of 5-bromo-1-(1-hydroxypropan-2-yl)pyridin-2(1H)-one (0.51 g, 2.2 mmol) and 2-thiopheneboronic acid (0.28 g, 2.2 mmol) in 30 mL of dioxane was added 6 mL of 1N Na2CO3 followed by 1,1′-bis(diphenylphosphino)ferrocene-palladium dichloride (0.16 g, 0.22 mmol). The reaction was heated to 90° C. for 12 hours. The mixture was then diluted with 30 mL of water and 80 mL of EtOAc. The organic phase was separated, washed with 40 mL of brine, dried over Na2SO4 and concentrated in vacuo. The residue was obtained as a greenish semi-solid (0.15 g, 29% yield). MS (ESI pos. ion) m/z (MH+): 236.0. Calc'd Exact Mass for C12H13NO2S: 235.07.

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US08314087B2
Source dataset	uspto-grants-2012_11
ORD ID	ord-78660626cb8848ea8030f6d17c3e4913
Source note	uspto-grants-2012_11