HuagongsheHuagongshe Chemistry Print Report · For research reference only
Di-tert-butyl azodicarboxylate → 4-{2-[2-(4-Chloro-phenyl)-5,6-difluoro-benzoimidazol-1-yl]-2-cyclohexyl-ethoxy}-3,5-difluoro-benzoic acid methyl ester
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Di-tert-butyl azodicarboxylate | HCID 97268 | — |
| Reactant | Methyl 3,5-difluoro-4-hydroxybenzoate | HCID 53847253 | — |
| Reactant | 2-[2-(4-Chloro-phenyl)-5,6-difluoro-benzoimidazol-1-yl]-2-cyclohexyl-ethanol | HCID 66619310 | — |
| Product | 4-{2-[2-(4-Chloro-phenyl)-5,6-difluoro-benzoimidazol-1-yl]-2-cyclohexyl-ethoxy}-3,5-difluoro-benzoic acid methyl ester | HCID 66619266 | 59% |
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), 3,5-difluoro-4-hydroxy-benzoic acid methyl ester (commercially available) and di-tert-butyl azodicarboxylate. 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) to give the desired compound as a light yellow foam (59%). MS (Turbo Spray): m/z=561.2 [M+H].
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US08088930B2 |
| Source dataset | uspto-grants-2012_01 |
| ORD ID | ord-bf3ae47bc00a4b58bef04be68f3a9252 |
| Source note | uspto-grants-2012_01 |