HuagongsheHuagongshe Chemistry Print Report · For research reference only
N,N'-Dimethylethylenediamine → 5-(4-tert-Butylphenyl)-1-(4-isopropoxyphenyl)indole-2-carboxylic acid ethyl ester
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | N,N'-Dimethylethylenediamine | HCID 8070 | — |
| Reactant | Potassium Phosphate, Tribasic | HCID 62657 | — |
| Reactant | 1-Bromo-4-(propan-2-yloxy)benzene | HCID 228088 | — |
| Reactant | Ethyl 5-(4-(tert-butyl)phenyl)-1H-indole-2-carboxylate | HCID 68475095 | — |
| Catalyst | Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI) | HCID 24350 | — |
| Solvent | Toluene | HCID 1140 | — |
| Solvent | Ethyl Acetate | HCID 8857 | — |
| Product | 5-(4-tert-Butylphenyl)-1-(4-isopropoxyphenyl)indole-2-carboxylic acid ethyl ester | HCID 68700341 | 95.1% |
Reaction Steps
5-(4-tert-Butylphenyl)indole-2-carboxylic acid ethyl ester (198 mg, 0.60 mmol; see step (a) above), CuI (12 mg, 0.06 mmol), K3PO4 (254 mg, 1.2 mmol), N,N′-dimethyl-1,2-diaminoethane (20 μL, 0.18 mmol) and 1-bromo-4-isopropoxybenzene (258 mg, 1.2 mmol) in toluene (2 mL) was heated at 110° C. for 17 h. The mixture was diluted with EtOAc and washed with NaHCO3 (aq. sat.), HCl (aq. 0.1 M), brine and then dried over Na2SO4. Concentration and purification by chromatography gave the sub-title compound (260 mg, 94%).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US07705023B2 |
| Source dataset | uspto-grants-2010_04 |
| ORD ID | ord-e2863fda51484e9780a671f7933b8df4 |
| Source note | uspto-grants-2010_04 |