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

HRID 2260616Notes

Reaction equation

HRID 2260616 reaction equation
[SH:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[N:7]([CH3:11])[C:6](=[O:12])[CH2:5]2.Cl[C:14]1[S:15][C:16]([C@@:19]2([OH:26])[CH2:24][CH2:23][O:22][C@@H:21]([CH3:25])[CH2:20]2)=[CH:17][N:18]=1>CN1C(=O)CCC1>[OH:26][C@:19]1([C:16]2[S:15][C:14]([S:1][C:2]3[CH:3]=[C:4]4[C:8](=[CH:9][CH:10]=3)[N:7]([CH3:11])[C:6](=[O:12])[CH2:5]4)=[N:18][CH:17]=2)[CH2:24][CH2:23][O:22][C@@H:21]([CH3:25])[CH2:20]1

Participants

4

Reactant 2

HCID 224137491-methyl-5-sulfanyl-2,3-dihydro-1H-indol-2-oneHCID 54155591(2S,4R)-4-(2-chlorothiazol-5-yl)-4-hydroxy-2-methyltetrahydropyran

Product 1

HCID 53849497(2S,4R)-4-hydroxy-2-methyl-4-[2-(1-methyl-2-oxoindolin-5-ylthio)thiazol-5-yl]tetrahydropyranYield 27%

Reagents, catalysts & solvents 1

HCID 13387N-methyl-2-pyrrolidoneSolvent

Procedure

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.;

Sources & evidence

ORD record
ord-958c69bfbf1347e0b7eeddd4d6fa1310
Source dataset
uspto-grants-1995_12
Patent number
US05478842

Reaction notes

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