N,N,N',N'-Tetramethylazodicarboxamide → 2-(3-{2-[2-(4-Chloro-phenyl)-5,6-difluoro-benzoimidazol-1-yl]-2-cyclohexyl-ethoxy}-phenoxy)-2-methyl-propionic acid ethyl ester

Participants

Role	Name	HCID	Charge
Reactant	N,N,N',N'-Tetramethylazodicarboxamide	HCID 4278	—
Reactant	Tributylphosphine	HCID 13831	—
Reactant	Ethyl 2-(3-hydroxyphenoxy)-2-methylpropanoate	HCID 46835528	—
Reactant	2-[2-(4-Chloro-phenyl)-5,6-difluoro-benzoimidazol-1-yl]-2-cyclohexyl-ethanol	HCID 66619310	—
Product	2-(3-{2-[2-(4-Chloro-phenyl)-5,6-difluoro-benzoimidazol-1-yl]-2-cyclohexyl-ethoxy}-phenoxy)-2-methyl-propionic acid ethyl ester	HCID 66619219	—

Reaction Steps

The title compound was prepared in analogy to Example 4, intermediate, from 2-[2-(4-chloro-phenyl)-5,6-difluoro-benzoimidazol-1-yl]-2-cyclohexyl-ethanol (Ex. 1, int. c), 2-(3-hydroxy-phenoxy)-2-methyl-propionic acid ethyl ester (CAS RN: 328919-24-0), tri-n-butylphosphin and N,N,N′,N′-tetramethylazodicarboxamide. The compound was purified by silica gel chromatography using a MPLC system (CombiFlash Companion, Isco Inc.) eluting with a gradient of n-heptane:ethyl acetate (100:0 to 70:30). Light yellow solid (19%). MS (Turbo Spray): m/z=597.2 [M+H].

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US08088930B2
Source dataset	uspto-grants-2012_01
ORD ID	ord-309084d44c8d492580770f3b344db576
Source note	uspto-grants-2012_01