HuagongsheHuagongshe Chemistry Print Report · For research reference only
Triethylamine → 4-[1-oxo-7-(3-[1,2,3]Triazol-1-ylprop-1-ynyl)-1H-6-azaisoquinolin-2-ylmethyl]benzoic Acid tert-Butyl Ester
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Triethylamine | HCID 8471 | — |
| Reactant | 1-(prop-2-yn-1-yl)-1H-imidazole | HCID 12591942 | — |
| Reactant | 4-(7-bromo-1-oxo-1H-6-azaisoquinolin-2-ylmethyl)benzoic acid tert-butyl ester | HCID 86591201 | — |
| Catalyst | Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI) | HCID 24350 | — |
| Catalyst | HCID 178418397 | HCID 178418397 | — |
| Solvent | Dimethylformamide | HCID 6228 | — |
| Product | 4-[1-oxo-7-(3-[1,2,3]Triazol-1-ylprop-1-ynyl)-1H-6-azaisoquinolin-2-ylmethyl]benzoic Acid tert-Butyl Ester | HCID 10252749 | — |
Reaction Steps
The coupling of 4-(7-bromo-1-oxo-1H-6-azaisoquinolin-2-ylmethyl)benzoic acid tert-butyl ester (0.70 g, 1.69 mmol) with 1-prop-2-ynyl-1H-imidazole (0.45 g, 4.22 mmol) using triethylamine (0.94 mL, 6.76 mmol), CuI (0.023 g, 0.12 mmol), and Pd(Ph3P)4 (0.08 g, 0.07 mmol) in dimethyl-formamide is carried out as described in Example 1, Step (2). The silica gel mesh is purified on a 3.5×18 cm silica gel column eluted with hexanes/ethyl acetate 1:1, methylene chloride/THF 7:1, then methylene chloride/THF 4:1. Evaporation and drying will afford the desired product.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US06977261B2 |
| Source dataset | uspto-grants-2005_12 |
| ORD ID | ord-5ea1c9927b4b4bdc86b118a9f33ad96a |
| Source note | uspto-grants-2005_12 |