Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Bromobenzene | HCID 7961 | — |
| Reactant | Potassium Phosphate, Tribasic | HCID 62657 | — |
| Reactant | Methyl indole-3-carboxylate | HCID 589098 | — |
| Reactant | trans-N,N'-dimethyl-1,2-cyclohexanediamine | HCID 2733821 | — |
| Catalyst | Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI) | HCID 24350 | — |
| Solvent | Toluene | HCID 1140 | — |
| Solvent | Aluminum | HCID 5359268 | — |
| Product | HCID 29923744 | HCID 29923744 | — |
Reaction Steps
A 5 mL screwtop vial containing methyl 1H-indole-3-carboxylate (100 mg, 0.571 mmol) and potassium phosphate (254 mg, 1.199 mmol) was degassed and purged with nitrogen after the addition of each of the following in sequential order: PhMe (1142 μl), bromobenzene (59.7 μl, 0.571 mmol), (1R,2R)—N1,N2-dimethylcyclohexane-1,2-diamine (54.4 μl, 0.342 mmol), and copper(I) iodide (32.6 mg, 0.171 mmol). The vial was sealed, wrapped in aluminum foil, and heated to 110° C. for 24 h. Concentration on silica gel and ISCO purification (20% EtOAc/hexanes) gave the title compound as a white solid.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|
| Patent number | US09303045B2 |
|---|
| Source dataset | uspto-grants-2016_04 |
|---|
| ORD ID | ord-dc40fdff76254aee8f27df88bdf28093 |
|---|
| Source note | uspto-grants-2016_04 |
|---|
