HuagongsheHuagongshe Chemistry Print Report · For research reference only
2-Propanethiol → 2'-Fluoro-2-isopropylsulfanyl-5'-methoxy-biphenyl-4-carboxylic acid methyl ester
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | 2-Propanethiol | HCID 6364 | — |
| Reactant | Diisopropylethylamine | HCID 81531 | — |
| Reactant | 1,1'-(9,9-Dimethyl-9H-xanthene-4,5-diyl)bis(1,1-diphenylphosphine) | HCID 636044 | — |
| Reactant | Methyl 2'-fluoro-2-iodo-5'-(methyloxy)-1,1'-biphenyl-4-carboxylate | HCID 57705628 | — |
| Catalyst | Bis(dibenzylideneacetone)palladium | HCID 9811564 | — |
| Solvent | Toluene | HCID 1140 | — |
| Product | 2'-Fluoro-2-isopropylsulfanyl-5'-methoxy-biphenyl-4-carboxylic acid methyl ester | HCID 57467638 | 89% |
Reaction Steps
A tube was charged with 66.15D (213 mg, 552 μmol), N-ethyl-N-isopropylpropan-2-amine (143 mg, 1103 μmol) and toluene, evacuated and back-filled with nitrogen three times. Pd2(dba)3, 4,5-bis(diphenylphosphino)-9,9-dimethyl-9H-xanthene (31.9 mg, 55.2 μmol) and propane-2-thiol (63.0 mg, 827 μmol) were added to the mixture and then the mixture was degassed three times. The suspension was refluxed overnight, filtered, and concentrated to give a residue which was purified by silica gel chromatography to give 69.24A as a pale yellow solid (164 mg, 89%). MS ESI m/e: 335.2 (M+1)+.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US08030354B2 |
| Source dataset | uspto-grants-2011_10 |
| ORD ID | ord-8019040c0c144d1d9586131756126d84 |
| Source note | uspto-grants-2011_10 |