Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Cesium carbonate | HCID 10796 | — |
| Reactant | 4-Bromo-1-(4-fluorophenyl)-1H-imidazole | HCID 22148033 | — |
| Reactant | [6s,9r,11r]2',3',4',5,5',6,7,8,9,10-Decahydro-2-(4,4,5,5-tetramethyl-[1,3,2]-dioxaborolan-2-yl)-5'-(2,2,2-trifluoroethyl)spiro[6,9-methanobenzocyclooctene-11,3'-[1,2,5]thiadiazole]1',1'-dioxide | HCID 23571079 | — |
| Catalyst | Tetrakis(triphenylphosphine)palladium | HCID 11979704 | — |
| Solvent | Water | HCID 962 | — |
| Solvent | Dimethylformamide | HCID 6228 | — |
| Solvent | Ethyl Acetate | HCID 8857 | — |
| Product | HCID 23571070 | HCID 23571070 | 12% |
Reaction Steps
To a degassed solution of 4-bromo-1-(4-fluorophenyl)imidazole from Step 1 (50 mg, 0.21 mmol) and the homochiral boronate from Example 24 Step 1 (100 mg. 0.21 mmol) in N,N-dimethylformamide (3 mL) and water (1 mL) was added cesium carbonate (67 mg, 0.21 mmol) followed by tetrakis(triphenylphosphine) palladium (0) (24 mg, 0.02 mmol). The reaction was heated at 100° C. for 19 hours. The cooled reaction mixture was diluted with ethyl acetate. The organic layer was washed with water (×3) and brine, dried (MgSO4) and concentrated. The residue was purified by flash chromatography on silica eluting with ethyl acetate/isohexane (gradient 20 to 30 to 50% to neat ethyl acetate) followed by recrystallisation from dichloromethane/diethyl ether to give the product (13 mg, 12%).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|
| Patent number | US07041689B2 |
|---|
| Source dataset | uspto-grants-2006_05 |
|---|
| ORD ID | ord-06cdbf6020774c1d8a7b54d0c03fb354 |
|---|
| Source note | uspto-grants-2006_05 |
|---|
