Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Propargyl alcohol | HCID 7859 | — |
| Reactant | HCID 66904783 | HCID 66904783 | — |
| Catalyst | Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI) | HCID 24350 | — |
| Catalyst | HCID 178418476 | HCID 178418476 | — |
| Solvent | triethylamine N,N-dimethylformamide | HCID 22056947 | — |
| Product | HCID 58485522 | HCID 58485522 | — |
Reaction Steps
120 mg (0.30 mmol) of N-[(3R)-1-azabicyclo[2.2.2]oct-3-yl]-6-bromo-1-benzothiophene-2-carboxamide hydrochloride (Example 11A), 10.5 mg (0.01 mmol) of PdCl2(PPh3)2 and 4.6 mg (0.02 mmol) of copper(I) iodide are dissolved in 1.5 ml of triethylamine/DMF (2:1) under argon and stirred at 60° C. for 1 h. Addition of 25.1 mg (0.45 mmol) of propargyl alcohol is followed by heating at 70° C. for a further 16 h. Cooling is followed by filtration through kieselguhr and purification by preparative HPLC, concentration and drying of the product under high vacuum. 12 mg (11% of theory) of the title compound are obtained.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|
| Patent number | US09067931B2 |
|---|
| Source dataset | uspto-grants-2015_06 |
|---|
| ORD ID | ord-a94034e77dbd43998ac27b62dbe5f3cd |
|---|
| Source note | uspto-grants-2015_06 |
|---|
