Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Methanol | HCID 887 | — |
| Reactant | Thionyl Chloride | HCID 24386 | — |
| Reactant | HCID 66620465 | HCID 66620465 | — |
| Product | HCID 66621285 | HCID 66621285 | 38% |
Reaction Steps
2-(2-Fluoro-4-(pyrrolidin-2-yl)phenyl)benzo[d]oxazole-7-carboxylic acid (500 mg, 1.53 mmol) was dissolved in methanol (20 mL) at −5° C.-0° C., thionyl chloride (0.2 mL, 2.40 mmol) was added dropwise. The mixture was heated at 70° C. for 3 h., then evaporated and the residue was adjusted to pH=9 by NaHCO3, and extracted with ethyl acetate. The organic layer was separated and washed with brine, dried over anhydrous sodium sulfate and evaporated to give methyl 2-(2-fluoro-4-(pyrrolidin-2-yl)phenyl)benzo[d]oxazole-7-carboxylate (200 mg, yield 38%) as white solid. LC-MS (ESI) m/z: 341 (M+1)+.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|
| Patent number | US08088760B2 |
|---|
| Source dataset | uspto-grants-2012_01 |
|---|
| ORD ID | ord-3680b0c74f9044889eb278ae12195aa6 |
|---|
| Source note | uspto-grants-2012_01 |
|---|