Cesium carbonate → 4-{3-Chloro-4-[2-(2-chloro-pyridin-4-yl)-3,3,3-trifluoro-2-hydroxy-1-methyl-propyl]-phenoxy}-3-fluoro-benzonitrile

Participants

Role	Name	HCID	Charge
Reactant	Cesium carbonate	HCID 10796	—
Reactant	3,4-Difluorobenzonitrile	HCID 587203	—
Reactant	3-Chloro-4-[2-(2-chloro-pyridin-4-yl)-3,3,3-trifluoro-2-hydroxy-1-methyl-propyl]-phenol	HCID 57421264	—
Solvent	Dimethylformamide	HCID 6228	—
Product	4-{3-Chloro-4-[2-(2-chloro-pyridin-4-yl)-3,3,3-trifluoro-2-hydroxy-1-methyl-propyl]-phenoxy}-3-fluoro-benzonitrile	HCID 86645954	—

Reaction Conditions

Temperature	120 °C

Reaction Steps

3,4-Difluorobenzonitrile (CAS Reg. No. 64248-62-0, 23 mg) and Cs2CO3 (13 mg) were added to a solution of 3-chloro-4-[2-(2-chloro-pyridin-4-yl)-3,3,3-trifluoro-2-hydroxy-1-methyl-propyl]-phenol (Example 19 step 5, 50 mg) in DMF (1 ml). The mixture was heated to 120° C. for 30 min in a microwave oven. The mixture was purified by prep. HPLC (C18-column, solvent gradient 30-98% CH3CN in 0.1% HCOOH[aq]) to give the title compound (43 mg) as a white foam. MS (m/e)=485.2 [M+H+].

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US08138189B2
Source dataset	uspto-grants-2012_03
ORD ID	ord-58c78cef08874961bbc1bc9976c26dcb
Source note	uspto-grants-2012_03