HuagongsheHuagongshe Chemistry Print Report · For research reference only
Water → 2-Cyano-2''-hydroxymethyl-4-methyl-[1,1';3',1'']terphenyl-5'-carboxylic acid ethyl ester
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Water | HCID 962 | — |
| Reactant | Cesium carbonate | HCID 10796 | — |
| Reactant | 2-(Hydroxymethyl)phenylboronic Acid | HCID 4374262 | — |
| Reactant | Methyl 5-bromo-2'-cyano-4'-methylbiphenyl-3-carboxylate | HCID 58449349 | — |
| Catalyst | Tetrabutylammonium Iodide | HCID 67553 | — |
| Solvent | Dimethylformamide | HCID 6228 | — |
| Product | 2-Cyano-2''-hydroxymethyl-4-methyl-[1,1';3',1'']terphenyl-5'-carboxylic acid ethyl ester | HCID 117666583 | — |
Reaction Steps
Into a 5 mL microwave vial were charged methyl 5-bromo-2′-cyano-4′-methylbiphenyl-3-carboxylate (95 mg, 0.29 mmol), 2-(hydroxymethyl)phenylboronic acid (87 mg, 0.57 mmol), cesium carbonate (466 mg, 1.43 mmol), tetra-n-butylammonium iodide (106 mg, 0.29 mmol), POPd (14 mg, 0.029 mmol), water (0.2 mL) and N,N-dimethylformamide (1 mL). The reaction mixture was subjected to microwave irradiation for 10 mins at 150° C. After cooling, the reaction mixture was extracted with ethylacetate. The organic layer was washed with brine, dried, and concentrated under reduced pressure to give the residue which was purified by HPLC to yield the title compound.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US09133122B2 |
| Source dataset | uspto-grants-2015_09 |
| ORD ID | ord-bd2fb6ee09e64b0cb4204b7179b23921 |
| Source note | uspto-grants-2015_09 |