HuagongsheHuagongshe Chemistry Print Report · For research reference only
Methyl 5-hydroxy-2-methylbenzoate → 5-(5-Biphenyl-4-yl-6-fluoro-1H-benzoimidazol-2-yloxy)-2-methyl-benzoic acid methyl ester
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Methyl 5-hydroxy-2-methylbenzoate | HCID 13929055 | — |
| Reactant | 5-Biphenyl-4-yl-6-fluoro-2-methanesulfonyl-1H-benzoimidazole | HCID 67445536 | — |
| Solvent | Pyridine | HCID 1049 | — |
| Solvent | Ethyl Acetate | HCID 8857 | — |
| Product | 5-(5-Biphenyl-4-yl-6-fluoro-1H-benzoimidazol-2-yloxy)-2-methyl-benzoic acid methyl ester | HCID 68524460 | — |
Reaction Steps
To a solution of 7 (454 mg, 1.2 mmol) in pyridine 10 mL was added 5-hydroxy-2-methyl-benzoic acid methyl ester (412 mg, 2.4 mmol). The reaction mixture was heated to reflux for 5 days. Once the reaction was determined to be complete by TLC, the reaction mixture was diluted with EtOAc (100 mL) and washed two times with 100 mL portions of saturated aqueous ammonium chloride. The combined organic layers were dried over MgSO4 filtered and concentrated in vacuo to give a crude brown oil. The resulting oil was purified on ISCO (EtOAc/Hexanes=2/3) to give title compound 8 as a yellow oil.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US08394969B2 |
| Source dataset | uspto-grants-2013_03 |
| ORD ID | ord-217096ef447c4e4baed7ac08e2efd5ce |
| Source note | uspto-grants-2013_03 |