Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Sodium Carbonate | HCID 10340 | — |
| Reactant | (3-Methoxyphenyl)boronic acid | HCID 2734370 | — |
| Reactant | HCID 66904783 | HCID 66904783 | — |
| Catalyst | Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+) | HCID 178418228 | — |
| Solvent | Dimethylformamide | HCID 6228 | — |
| Product | HCID 67314871 | HCID 67314871 | — |
Reaction Steps
0.3 ml of 2 M aqueous sodium carbonate solution and 4.1 mg (0.005 mmol) of PdCl2(dppf) are added to a mixture of 40 mg (0.10 mmol) of N-[(3R)-1-azabicyclo[2.2.2]oct-3-yl]-6-bromo-1-benzothiophene-2-carboxamide hydrochloride (Example 11A) and 15.1 mg (0.10 mmol) of 3-methoxyphenylboronic acid in 1 ml of DMF. The reaction mixture is heated at 80° C. for 14 h, filtered through kieselguhr and evaporated to dryness. Purification of the crude product by preparative HPLC, subsequent addition of 1N hydrochloric acid and drying under high vacuum result in 25.5 mg (57% 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-79f9815865b7474b810c527c86e1a467 |
|---|
| Source note | uspto-grants-2015_06 |
|---|
