HuagongsheHuagongshe Chemistry Print Report · For research reference only
Potassium Carbonate → Methyl 7-(4-((4-chlorophenethyl)carbamoyl)phenoxy)-6-cyano-2,2-dimethylchroman-4-carboxylate
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Potassium Carbonate | HCID 11430 | — |
| Reactant | N-(4-chlorophenethyl)-4-hydroxybenzamide | HCID 60628097 | — |
| Reactant | Methyl 6-cyano-7-fluoro-2,2-dimethylchroman-4-carboxylate | HCID 67080271 | — |
| Solvent | N-methyl-2-pyrrolidone | HCID 13387 | — |
| Product | Methyl 7-(4-((4-chlorophenethyl)carbamoyl)phenoxy)-6-cyano-2,2-dimethylchroman-4-carboxylate | HCID 67080218 | 5.4% |
Reaction Conditions
| Temperature | 110 °C |
|---|
Reaction Steps
Methyl 6-cyano-7-fluoro-2,2-dimethylchroman-4-carboxylate (19 mg, 0.072 mmol) was diluted with N-methylpyrrolidone (2 mL) followed by the addition of K2CO3 (25 mg, 0.18 mmol) and N-(4-chlorophenethyl)-4-hydroxybenzamide (20 mg, 0.072 mmol). The reaction was bubbled with argon for 10 minutes and then heated at 110° C. for 6 hours. After cooling, the reaction mixture was loaded directly onto a Biotage 25 column and eluted with 5% ethyl acetate/hexanes to 100% ethyl acetate to yield the title compound (2.0 mg, 5.3% yield).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US08569522B2 |
| Source dataset | uspto-grants-2013_10 |
| ORD ID | ord-eb18c3cadb7245b2adcc6d293a370a1a |
| Source note | uspto-grants-2013_10 |