Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Dichloromethane | HCID 6344 | — |
| Reactant | Sodium Carbonate | HCID 10340 | — |
| Reactant | 4-Aminophenylboronic acid | HCID 2734615 | — |
| Reactant | Methyl 3-bromo-2-fluorobenzoate | HCID 21584505 | — |
| Solvent | Water | HCID 962 | — |
| Solvent | 1,2-Dimethoxyethane | HCID 8071 | — |
| Product | HCID 68194460 | HCID 68194460 | — |
Reaction Steps
To a solution of Example 223A (3.1 g, 13 mmol) in dimethoxyethane (25 mL) was added (4-aminophenyl)boronic acid (2.77 g, 16 mmol) and Na2CO3 (3.38 g, 31.2 mmol) in water (6 mL) followed by 1′-bis(diphenylphosphino)ferrocene-palladium(II)dichloride:dichloromethane:complex (652 mg, 0.8 mmol). The mixture was heated to 85° C. for 10 hours. After cooling to room temperature, the reaction mixture was partitioned between water and ethyl acetate. The organic phase was washed with water followed by brine then dried over magnesium sulfate. After filtration and concentration, the crude product was purified by flash chromatography (1%-100% ethyl acetate/hexane) to provide the title compound.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|
| Patent number | US08710065B2 |
|---|
| Source dataset | uspto-grants-2014_04 |
|---|
| ORD ID | ord-4af63ec729424a6c83bc2e0da4932835 |
|---|
| Source note | uspto-grants-2014_04 |
|---|