Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Sodium Carbonate | HCID 10340 | — |
| Reactant | 2,5-Dimethoxyphenylboronic acid | HCID 2734342 | — |
| Reactant | N-[(3R)-1-azabicyclo[2.2.2]oct-3-yl]-7-bromo-1-benzofuran-2-carboxamide hydrochloride | HCID 67313982 | — |
| Catalyst | Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+) | HCID 178418228 | — |
| Solvent | Dimethylformamide | HCID 6228 | — |
| Product | HCID 67313826 | HCID 67313826 | — |
Reaction Steps
0.78 ml of 2 M aqueous sodium carbonate solution and 21.2 mg (0.03 mmol) of PdCl2(dppf) are added to a mixture of 200 mg (0.52 mmol) of N-[(3R)-1-azabicyclo[2.2.2]oct-3-yl]-7-bromo-1-benzofuran-2-carboxamide hydrochloride (Example 30A) and 94.4 mg (0.52 mmol) of 2,5-dimethoxyphenylboronic acid in 2 ml of DMF. The reaction mixture is heated at 70° C. for 17 h and then filtered through kieselguhr and evaporated to dryness. Purification of the crude product by preparative HPLC, subsequent addition of a 3:1 mixture of methanol and 1N hydrochloric acid, concentration and drying under high vacuum result in 75 mg (31.7% of theory) of the title compound.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|
| Patent number | US09067931B2 |
|---|
| Source dataset | uspto-grants-2015_06 |
|---|
| ORD ID | ord-cdd311ac1ec74a32926d398ebf0be998 |
|---|
| Source note | uspto-grants-2015_06 |
|---|
