Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Methanol | HCID 887 | — |
| Reactant | Sodium Carbonate | HCID 10340 | — |
| Reactant | 3-Carboxyphenylboronic acid | HCID 2733957 | — |
| Reactant | HCID 67411147 | HCID 67411147 | — |
| Catalyst | Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+) | HCID 178418228 | — |
| Solvent | Water | HCID 962 | — |
| Solvent | Dimethylformamide | HCID 6228 | — |
| Product | HCID 71115280 | HCID 71115280 | 70.2% |
Reaction Steps
To a solution of Intermediate 16 (35 g, 0.086 mol, 1.0 eq) and 3-carboxyphenylboronic acid (14.27 g, 0.086, 1.0 eq) in DMF (350 ml) and H2O (87.5 ml) was added Na2CO3 (18.2 g, 0.172 mol, 2.0 eq). Then Pd(dppf)Cl2 (3.15 g, 0.0043 mol, 0.05 eq) was added to the solution under N2. The resulting solution was stirred at 100° C. for 16 hrs. Solvent was evaporated under vacuum and the residue was purified by column chromatography on silica gel using DCM: MeOH=10:1 to give the title compound (27 g, 70% yield) as brown solid.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|
| Patent number | US08912209B2 |
|---|
| Source dataset | uspto-grants-2014_12 |
|---|
| ORD ID | ord-4350c83938ae484cbdb156a8382229fc |
|---|
| Source note | uspto-grants-2014_12 |
|---|
