Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Diisopropylamine | HCID 7912 | — |
| Reactant | Trimethylsilylacetylene | HCID 66111 | — |
| Reactant | 4-[(4-Iodophenyl)carbonyl]morpholine | HCID 772634 | — |
| Catalyst | Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI) | HCID 24350 | — |
| Catalyst | HCID 178418476 | HCID 178418476 | — |
| Solvent | Tetrahydrofuran | HCID 8028 | — |
| Product | HCID 69292920 | HCID 69292920 | 99.8% |
Reaction Steps
To a mixture under Ar of (4-iodo-phenyl)-morpholin-4-yl-methanone (273 mg), trimethylsilylacetylene (169 mg), [PdCl2(PPh3)2] (30 mg) and copper(i) iodide (15 mg) is added a degassed mixture of THF (4.5 ml) and diisopropylamine (4.5 ml). After stirring over night at 57° C. and aqueous work up, the organic layer is dried over Na2SO4 and the solvent is evaporated. Flash chromatography (silica gel, CH2Cl2/MeOH/25% NH4OH 97:3:0.3) yields 247 mg of morpholin-4-yl-(4-trimethylsilanylethynyl-phenyl)-methanone as a light brown solid, 1H-NMR (300 MHz): 0.26 (s, 3H); 3.32-3.91 (br, 8H); 7.34 (d, J=6.5, 2H); 7.51 (d, J=6.5, 2H).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|
| Patent number | US07459480B2 |
|---|
| Source dataset | uspto-grants-2008_12 |
|---|
| ORD ID | ord-c2682053f70748b6b86aecf1328d9aab |
|---|
| Source note | uspto-grants-2008_12 |
|---|
