HuagongsheHuagongshe Chemistry Print Report · For research reference only
Triethylamine → [3-(5-biphenyl-4-yl-6-fluoro-1H-benzoimidazol-2-yloxy)-phenyl]-phosphonic acid diisopropyl ester
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Triethylamine | HCID 8471 | — |
| Reactant | Triethylsilane | HCID 12052 | — |
| Reactant | Phosphorous acid, bis(1-methylethyl) ester | HCID 21884976 | — |
| Reactant | 5-Biphenyl-4-yl-2-(3-bromo-phenoxy)-6-fluoro-1H-benzoimidazole | HCID 67446383 | — |
| Catalyst | Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+) | HCID 178418228 | — |
| Solvent | Toluene | HCID 1140 | — |
| Solvent | Dimethylformamide | HCID 6228 | — |
| Solvent | Ethyl Acetate | HCID 8857 | — |
| Product | [3-(5-biphenyl-4-yl-6-fluoro-1H-benzoimidazol-2-yloxy)-phenyl]-phosphonic acid diisopropyl ester | HCID 86658719 | — |
Reaction Steps
To a microwave reactor vial was added compound 13-7 (107 mg, 0.23 mmol), PdCl2(dppf) (34 mg, 0.047 mmol), triethylamine (0.1 mL, 0.69 mmol), triethylsilane (15 μL, 0.092 mmol), diisopropylphosphite (46 μL, 0.28 mmol) in 3 mL of toluene and 0.5 mL of DMF. The reaction was run in a microwave reactor for 7 min at 140° C. The reaction mixture was diluted with EtOAc (50 mL) and washed three times with 50 mL portions of saturated aqueous ammonium chloride. The combined organic layers were dried over MgSO4 filtered and concentrated in vacuo. The resulting residue was purified by silica gel column chromatography (eluting with EtOAc/Hexanes=4/1) to yield title compound 13-8 as a brown oil.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US08410284B2 |
| Source dataset | uspto-grants-2013_04 |
| ORD ID | ord-4115b0955075453c8e912a2df20138a1 |
| Source note | uspto-grants-2013_04 |