HuagongsheHuagongshe Chemistry Print Report · For research reference only
Trimethylsilylacetylene → tert-butyl-N-[1-oxo-1-[[1-(2-trimethylsilylethynyl)isoquinolin-3-yl]amino]-propan-2-yl]carbamate
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Trimethylsilylacetylene | HCID 66111 | — |
| Reactant | Diisopropylethylamine | HCID 81531 | — |
| Reactant | tert-butyl-N-[1-[(1-bromoisoquinolin-3-yl)amino]-1-oxopropan-2-yl]carbamate | HCID 86694369 | — |
| Catalyst | Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI) | HCID 24350 | — |
| Catalyst | HCID 178418476 | HCID 178418476 | — |
| Solvent | N-methyl-2-pyrrolidone | HCID 13387 | — |
| Product | tert-butyl-N-[1-oxo-1-[[1-(2-trimethylsilylethynyl)isoquinolin-3-yl]amino]-propan-2-yl]carbamate | HCID 86694376 | — |
Reaction Steps
A mixture of tert-butyl-N-[1-[(1-bromoisoquinolin-3-yl)amino]-1-oxopropan-2-yl]-carbamate B4a (500 mg, 1.27 mmol), ethynyl(trimethyl)silane (137 mg, 1.4 mmol), copper(I) iodide (23 mg, 0.12 mmol), Dichlorobis(triphenylphosphine)palladium(II) (90 mg, 0.13 mmol) and DIPEA (700 μl, 4.12 mmol) is stirred under argon atmosphere in NMP (4 ml) for 1 h at 80° C. The mixture is concentrated in vacuo and the product purified by RP HPLC. Yield: 319 mg (61%). HPLC-MS: M+H=412; tR=2.11 min (*Method—4).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US08859541B2 |
| Source dataset | uspto-grants-2014_10 |
| ORD ID | ord-8f12aeee77de44f88f15d4c0fbacccd3 |
| Source note | uspto-grants-2014_10 |