Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Ethyl Acetate | HCID 8857 | — |
| Reactant | Potassium Acetate | HCID 517044 | — |
| Reactant | 4-Bromo-2-methylpyridine | HCID 2762835 | — |
| Reactant | HCID 67435246 | HCID 67435246 | — |
| Catalyst | palladium(II) acetate | HCID 167845 | — |
| Solvent | Dimethylacetamide | HCID 31374 | — |
| Product | HCID 67536812 | HCID 67536812 | — |
Reaction Steps
Under argon, 200 mg (0.90 mmol) of 2-isopropyl-4-(4-fluorophenyl)-1,3-thiazole, 77 mg (0.45 mmol) of 4-bromo-2-methylpyridine, 133 mg (1.35 mmol) of potassium acetate and 0.4 mg (2 μmol) of palladium(II) acetate in 5 ml of DMA are heated to 150° C. After 3 h, 50 ml of ethyl acetate are added and the reaction mixture is filtered through a silica gel cartridge. 10 ml of water are added to the filtrate. The organic phase is separated off, washed once more with 10 ml of water, dried over MgSO4 and concentrated under reduced pressure. The residue is purified by column chromatography on silica gel (cyclohexane/ethyl acetate). This gives 115 mg (41%) of the desired product; 1H-NMR(DMSO-(D6) δ: 8.39 (d, 1H), 7.48 (m, 2H), 7.22 (m, 2H), 7.17 (s, 1H), 7.03 (d, 1H), 3.35 (m, 1H), 2.43 (s, 3H), 1.39 (d, 6H).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|
| Patent number | US09198426B2 |
|---|
| Source dataset | uspto-grants-2015_12 |
|---|
| ORD ID | ord-f45645d5764e4cfbbdbf52bc73011a2f |
|---|
| Source note | uspto-grants-2015_12 |
|---|