2-Fluoro-4-nitrophenol → 2-(5-(1,3-Dioxan-2-yl)-1-methyl-1H-imidazol-2-yl)-7-(2-fluoro-4-nitrophenoxy)thieno[3,2-b]pyridine

Participants

Role	Name	HCID	Charge
Reactant	2-Fluoro-4-nitrophenol	HCID 9825	—
Reactant	Sodium Bicarbonate	HCID 516892	—
Reactant	2-(5-(1,3-Dioxan-2-yl)-1-methyl-1H-imidazol-2-yl)-7-chlorothieno[3,2-b]pyridine	HCID 57919499	—
Solvent	Dichloromethane	HCID 6344	—
Solvent	Diphenyl Ether	HCID 7583	—
Product	2-(5-(1,3-Dioxan-2-yl)-1-methyl-1H-imidazol-2-yl)-7-(2-fluoro-4-nitrophenoxy)thieno[3,2-b]pyridine	HCID 57919527	31.2%

Reaction Conditions

Temperature	180 °C

Reaction Steps

A mixture of 40 (5.9 g, 17.57 mmol), 2-fluoro-4-nitrophenol (5.52 g, 35.1 mmol) and NaHCO3 (1.346 g, 16.02 mmol) in Ph2O (7 mL) was heated to 180° C. for 4 hours. The reaction mixture was cooled to RT and diluted with DCM, filtered and concentrated. Purification of the residue by column chromatography (eluent EtOAc) afforded 41 (2.5 g, 31% yield) as a yellow solid. MS (m/z): 457.1 (M+H).

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US08846927B2
Source dataset	uspto-grants-2014_09
ORD ID	ord-e1a7d28874144d41bdc7e97b26018276
Source note	uspto-grants-2014_09