HuagongsheHuagongshe Chemistry Print Report · For research reference only
1-methyl-5-sulfanyl-2,3-dihydro-1H-indol-2-one → (2S,4R)-4-hydroxy-2-methyl-4-[2-(1-methyl-2-oxoindolin-5-ylthio)thiazol-5-yl]tetrahydropyran
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | 1-methyl-5-sulfanyl-2,3-dihydro-1H-indol-2-one | HCID 22413749 | — |
| Reactant | (2S,4R)-4-(2-chlorothiazol-5-yl)-4-hydroxy-2-methyltetrahydropyran | HCID 54155591 | — |
| Solvent | N-methyl-2-pyrrolidone | HCID 13387 | — |
| Product | (2S,4R)-4-hydroxy-2-methyl-4-[2-(1-methyl-2-oxoindolin-5-ylthio)thiazol-5-yl]tetrahydropyran | HCID 53849497 | 27% |
Reaction Steps
Using an analogous procedure to that described in Example 26 except that NMP was used in place of DMF as reaction solvent, 5-mercapto-1-methylindolin-2-one was reacted with (2S,4R)-4-(2-chlorothiazol-5-yl)-4-hydroxy-2-methyltetrahydropyran to give (2S,4R)-4-hydroxy-2-methyl-4-[2-(1-methyl-2-oxoindolin-5-ylthio)thiazol-5-yl]tetrahydropyran in 27% yield, m.p. 140° C.;
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US05478842 |
| Source dataset | uspto-grants-1995_12 |
| ORD ID | ord-958c69bfbf1347e0b7eeddd4d6fa1310 |
| Source note | uspto-grants-1995_12 |