Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Ethyl Acetate | HCID 8857 | — |
| Reactant | Diisopropylethylamine | HCID 81531 | — |
| Reactant | Sodium methanethiolate | HCID 4378561 | — |
| Reactant | HCID 118054559 | HCID 118054559 | — |
| Catalyst | 1,1'-(9,9-Dimethyl-9H-xanthene-4,5-diyl)bis(1,1-diphenylphosphine) | HCID 636044 | — |
| Catalyst | Bis(dibenzylideneacetone)palladium | HCID 9811564 | — |
| Solvent | Toluene | HCID 1140 | — |
| Product | HCID 118045363 | HCID 118045363 | 102% |
Reaction Steps
A mixture of Xantphos (13.91 mg, 0.024 mmol), Pd2(dba)3 (22.02 mg, 0.024 mmol), (5)-tert-butyl 4-(3-bromo-5-fluorophenyl)-2,2-dimethyloxazolidine-3-carboxylate (300 mg, 0.802 mmol), DIEA (700 μl, 4.01 mmol) and sodium methanethiolate (112 mg, 1.603 mmol) in toluene (2.6 mL) was microwave heated at 110° C. for 18 min. EtOAc was added, and washed with sat NaHCO3, water, and brine. The mixture was filtered off, concentrated and purified with flash chromatography eluting with 0-60% of EtOAc/heptane to provide (S)-tert-butyl 4-(3-fluoro-5-(methylthio)phenyl)-2,2-dimethyloxazolidine-3-carboxylate (278 mg, 102%) as an oil. LCMS (m/z): 286.1 (MH+-56), 1.14 min.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|
| Patent number | US09242996B2 |
|---|
| Source dataset | uspto-grants-2016_01 |
|---|
| ORD ID | ord-6a49e12b1aa64551aeaabd25e8069136 |
|---|
| Source note | uspto-grants-2016_01 |
|---|
