HuagongsheHuagongshe Chemistry Print Report · For research reference only
Diisopropylethylamine → Propyl [7-(4-benzyl-1H-1,2,3-triazol-1-yl)-6,7,8,9-tetrahydropyrido[1,2-a]indol-10-yl]acetate
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Diisopropylethylamine | HCID 81531 | — |
| Reactant | Benzylacetylene | HCID 575753 | — |
| Reactant | Propyl (7-azido-6,7,8,9-tetrahydropyrido[1,2-a]indol-10-yl)acetate | HCID 59487226 | — |
| Catalyst | Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI) | HCID 24350 | — |
| Solvent | Tetrahydrofuran | HCID 8028 | — |
| Product | Propyl [7-(4-benzyl-1H-1,2,3-triazol-1-yl)-6,7,8,9-tetrahydropyrido[1,2-a]indol-10-yl]acetate | HCID 86645391 | — |
Reaction Steps
To a stirred solution of propyl (7-azido-6,7,8,9-tetrahydropyrido[1,2-a]indol-10-yl)acetate (1 eq) (Synthesis described in WO07019675 A1) and prop-2-yn-1-ylbenzene (2 eq) in tetrahydrofuran (THF) (0.1M) at room temperature was added diisopropyl ethylamine (DIPEA) (5 eq) and CuI (5 eq). The reaction mixture was stirred overnight then quenched with NH4Cl sat and extracted with ethyl acetate (EA), washed with brine, dried over Na2SO4 and evaporated. Purification by combi-flash EA/Hex 0-100% afforded the desired compound which was used directly for next step.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US08394819B2 |
| Source dataset | uspto-grants-2013_03 |
| ORD ID | ord-968e6740638a412e9dbe8b972029b298 |
| Source note | uspto-grants-2013_03 |