Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Triethylamine | HCID 8471 | — |
| Reactant | Potassium Carbonate | HCID 11430 | — |
| Reactant | 1-Bromo-2-chlorobenzene | HCID 12754 | — |
| Reactant | HCID 54049466 | HCID 54049466 | — |
| Catalyst | Palladium | HCID 23938 | — |
| Catalyst | Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI) | HCID 24350 | — |
| Solvent | Dimethylformamide | HCID 6228 | — |
| Product | HCID 53679748 | HCID 53679748 | — |
Reaction Steps
250 mg of 6-ethinyl-4-methoxymethyl-β-carboline-3-carboxylic acid isopropyl ester is mixed in 8 ml of dimethylformamide with 2 ml of triethylamine, 118 mg of anhydrous potassium carbonate, 22 mg of tetrakis (triphenylphosphine)-palladium(O), 7 mg of copper(I)iodide and 149 mg of 4-bromochlorobenzone and then the mixture is heated for 4 hours to 110° C. Then bromochlorobenzene, copper(I)iodide and palladium catalyst are added again and heated for 3 hours to 120° C. solution temperature. After concentration by evaporation it is taken up in ethyl acetate, washed in succession with saturated sodium carbonate and common salt solution each, dried, filtered and concentrated by evaporation. The residue is chromatographed twice in succession on silica gel, first with the mobile solvent toluene:ethanol:water=80:20:1 and then with the mobile solvent methylene chloride:ethanol=12:1, and the corresponding fractions are combined and used in the next chromatography. 120 mg of 6-(4-chlorophenylethinyl)-4-methoxymethyl-β-carboline-3-carboxylic acid isopropyl ester, melting point of 220°-221° C., is obtained.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US05506234 |
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| Source dataset | uspto-grants-1996_04 |
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| ORD ID | ord-ebb4163673894631bdf9d0cf1be7ad86 |
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| Source note | uspto-grants-1996_04 |
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