HuagongsheHuagongshe Chemistry Print Report · For research reference only
Potassium Carbonate → 4'-(2,6-Difluoro-benzoylamino)-6-methyl-biphenyl-3-carboxylic acid methyl ester
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Potassium Carbonate | HCID 11430 | — |
| Reactant | Methyl 3-bromo-4-methylbenzoate | HCID 7015747 | — |
| Reactant | 2,6-difluoro-N-[4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl]benzamide | HCID 53414211 | — |
| Solvent | N-methyl-2-pyrrolidone | HCID 13387 | — |
| Product | 4'-(2,6-Difluoro-benzoylamino)-6-methyl-biphenyl-3-carboxylic acid methyl ester | HCID 11552658 | 75% |
Reaction Conditions
| Temperature | 120 °C |
|---|
Reaction Steps
A suspension of 2,6-difluoro-N-[4-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-phenyl]-benzamide (359 mg, 1 mmol), 3-bromo-4-methyl-benzoic acid methyl ester (228 mg, 1 mmol), benzyl(chloro)bis(triphenylphosphine)palladium (38 mg, 0.05 mmol) and K2CO3 (690 mg, 5 mmol) in 1-methylpyrrolidinone (NMP) (5 ml) was degassed with vacuum and heated at 120° C. for 10 hr. After cooling down to room temperature, ethyl acetate (EtOAc) (200 ml) was added and the mixture was washed with water (60 ml×3). The EtOAc was evaporated and the residue was purified by column chromatography on silica gel (Hexanes:EtOAc) to give Compound 1 (286 mg, yield 75%).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US08592486B2 |
| Source dataset | uspto-grants-2013_11 |
| ORD ID | ord-8afd4206935246eb92863eb593fc3d1b |
| Source note | uspto-grants-2013_11 |