HuagongsheHuagongshe Chemistry Print Report · For research reference only
[4-(tert-Butyldimethylsilanyloxy)cyclohexyl]-(2-cyclopropylethynylphenyl)amine → 1-[4-(tert-Butyldimethylsilanyloxy)cyclohexyl]-2-cyclopropyl-1H-indole
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | [4-(tert-Butyldimethylsilanyloxy)cyclohexyl]-(2-cyclopropylethynylphenyl)amine | HCID 57675733 | — |
| Catalyst | Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI) | HCID 24350 | — |
| Solvent | Dimethylformamide | HCID 6228 | — |
| Product | 1-[4-(tert-Butyldimethylsilanyloxy)cyclohexyl]-2-cyclopropyl-1H-indole | HCID 57675761 | — |
Reaction Steps
To a solution of [4-(tert-butyldimethylsilanyloxy)cyclohexyl]-(2-cyclopropylethynylphenyl)amine (3.84 g, 10.4 mmol) in N,N-dimethylformamide (60 mL) was added copper(I) iodide (100 mg, 0.525 mmol). After the reaction was refluxed for 48 hours, it was allowed to cool to room temperature, and the solvent was removed in vacuo. The residue was partitioned between water and dichloromethane. The dichloromethane was dried (MgSO4) and concentrated to give a dark residue that was used in the next step with no further purification. LC-MS (C23H35NOSi calc'd 369) m/z 370 (M+H).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US08129424B2 |
| Source dataset | uspto-grants-2012_03 |
| ORD ID | ord-5a6ba791f2c841d68d6fb3c6d3288391 |
| Source note | uspto-grants-2012_03 |