Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Sodium Carbonate | HCID 10340 | — |
| Reactant | [3-(Hydroxymethyl)phenyl]boronic acid | HCID 2734662 | — |
| Reactant | N-[(3R)-1-azabicyclo[2.2.2]oct-3-yl]-7-bromo-1-benzothiophene-2-carboxamide hydrochloride | HCID 66904832 | — |
| Catalyst | Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+) | HCID 178418228 | — |
| Solvent | Dimethylformamide | HCID 6228 | — |
| Product | HCID 67314228 | HCID 67314228 | — |
Reaction Steps
200 mg (0.45 mmol) of N-[(3R)-1-azabicyclo[2.2.2]oct-3-yl]-7-bromo-1-benzothiophene-2-carboxamide hydrochloride (Example 8A) and 74.6 mg (0.49 mmol) of 3-(hydroxymethyl)phenylboronic acid are introduced into 3 ml of DMF. Addition of 0.67 ml of 2 M sodium carbonate solution and 1.8.2 mg (0.02 mmol) of PdCl2(dppf) is followed by heating to 80° C. After 14 h, the reaction mixture is filtered through kieselguhr and purified by separation by preparative HPLC. The product fractions are concentrated and, after addition of a 5:1 mixture of methanol and 4N hydrogen chloride in dioxane, again concentrated. Drying under high vacuum results in 40 mg (19% of theory) of the title compound.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|
| Patent number | US07977485B2 |
|---|
| Source dataset | uspto-grants-2011_07 |
|---|
| ORD ID | ord-4e588697a2264f98ac8e3c7fa8e22a11 |
|---|
| Source note | uspto-grants-2011_07 |
|---|
