HuagongsheHuagongshe Chemistry Print Report · For research reference only
Triphenylphosphine → 4-[(2-Bromo-4-thiazolyl)methoxy]-1-(2-cyclopropyl-3-methylimidazo[1,2-a]pyridin-6-yl)-2(1h)-pyridinone
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Triphenylphosphine | HCID 11776 | — |
| Reactant | (2-Bromo-1,3-thiazol-4-yl)methanol | HCID 2763211 | — |
| Reactant | 2-methoxyethyl N-(2-methoxyethoxycarbonylimino)carbamate | HCID 53384415 | — |
| Reactant | 1-(2-Cyclopropyl-3-methylimidazo[1,2-a]pyridin-6-yl)-4-hydroxypyridin-2(1H)-one | HCID 89690281 | — |
| Solvent | Tetrahydrofuran | HCID 8028 | — |
| Solvent | Ethyl Acetate | HCID 8857 | — |
| Product | 4-[(2-Bromo-4-thiazolyl)methoxy]-1-(2-cyclopropyl-3-methylimidazo[1,2-a]pyridin-6-yl)-2(1h)-pyridinone | HCID 121386240 | 47.6% |
Reaction Steps
To a solution of 1-(2-cyclopropyl-3-methylimidazo[1,2-a]pyridin-6-yl)-4-hydroxypyridin-2(1H)-one (239 mg), (2-bromothiazol-4-yl)methanol (330 mg) and triphenylphosphine (669 mg) in THF (5 ml) was added bis(2-methoxyethyl) azodicarboxylate (597 mg), and the mixture was stirred at room temperature for 3 h. The mixture was diluted with EtOAc, washed with water and brine successively, concentrated in vacuo, and purified by silica gel column chromatography (EtOAc/MeOH) to give the title compound (185 mg) as a white solid.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US09365540B2 |
| Source dataset | uspto-grants-2016_06 |
| ORD ID | ord-f07cf830a60242708f797f2ea6fbaf60 |
| Source note | uspto-grants-2016_06 |