Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Acetonitrile | HCID 6342 | — |
| Reactant | Triethylamine | HCID 8471 | — |
| Reactant | 1-(Difluoromethoxy)-4-iodobenzene | HCID 2737008 | — |
| Reactant | tert-Butyl 3-ethynylphenylcarbamate | HCID 11275982 | — |
| Catalyst | Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI) | HCID 24350 | — |
| Catalyst | HCID 178418476 | HCID 178418476 | — |
| Solvent | Ethyl Acetate | HCID 8857 | — |
| Product | HCID 59305375 | HCID 59305375 | 100% |
Reaction Steps
A mixture of (3-ethynyl-phenyl)-carbamic acid tert-butyl ester (14.7 g, 67.7 mmol), 1-difluoromethoxy-4-iodo-benzene (18.2 g, 67.7 mmol), NEt3 (47 mL, 338 mmol), acetonitrile (225 mL), CuI (1.29 g, 6.77 mmol), and Pd(PPh3)2Cl2 (2.85 g, 4.05 mmol) was heated to 60° C. for 1 h. The reaction was diluted with EtOAc/Hex (1:10) and then passed through a pad of silica gel and concentrated and purified with chromatography using hexanes/ethyl acetate (10:1) as the eluting solvents gave the title compound (24.3 g, 100%), characterized by NMR and mass spectral analyses.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|
| Patent number | US07723368B2 |
|---|
| Source dataset | uspto-grants-2010_05 |
|---|
| ORD ID | ord-12a06630d88a42338b6a01cba6fc25ae |
|---|
| Source note | uspto-grants-2010_05 |
|---|
