1-methyl-5-sulfanyl-2,3-dihydro-1H-indol-2-one → (2S,4R)-4-hydroxy-2-methyl-4-[3-(1-methyl-2-oxoindolin-5-ylthio)phenyl]tetrahydropyran

HRID 2260614Notes

Reaction equation

HRID 2260614 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.[OH:13][C@:14]1([C:21]2[CH:26]=[CH:25][CH:24]=[C:23](I)[CH:22]=2)[CH2:19][CH2:18][O:17][C@@H:16]([CH3:20])[CH2:15]1>>[OH:13][C@:14]1([C:21]2[CH:26]=[CH:25][CH:24]=[C:23]([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)[CH:22]=2)[CH2:19][CH2:18][O:17][C@@H:16]([CH3:20])[CH2:15]1

Participants

3

Reactant 2

HCID 224137491-methyl-5-sulfanyl-2,3-dihydro-1H-indol-2-oneHCID 54517626(2S,4R)-4-hydroxy-4-(3-iodophenyl)-2-methyltetrahydropyran

Product 1

HCID 54441772(2S,4R)-4-hydroxy-2-methyl-4-[3-(1-methyl-2-oxoindolin-5-ylthio)phenyl]tetrahydropyranYield 55%

Procedure

Using an analogous procedure to that described in Example 6, 5-mercapto-1-methylindolin-2-one was reacted with (2S,4R)-4-hydroxy-4(3-iodophenyl)-2-methyltetrahydropyran to give (2S,4R)-4-hydroxy-2-methyl-4-[3-(1-methyl-2-oxoindolin-5-ylthio)phenyl]tetrahydropyran in 55% yield, m.p. 110°-111° C. (recrystallised from a mixture of diethyl ether and ethyl acetate);

Sources & evidence

ORD record
ord-37457d662dfa42d6808dafa1aade6be1
Source dataset
uspto-grants-1995_12
Patent number
US05478842

Reaction notes

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