5-chloro-1H-indole-2,3-dione → 3-[4-({[tert-butyl(dimethyl)silyl]oxy}methyl)-2-methoxyphenyl]-5-chloro-3-hydroxy-1,3-dihydro-2H-indol-2-one

HRID 1662772Notes

Reaction equation

HRID 1662772 reaction equation
Br[C:2]1[CH:16]=[CH:15][C:5]([CH2:6][O:7][Si:8]([C:11]([CH3:14])([CH3:13])[CH3:12])([CH3:10])[CH3:9])=[CH:4][C:3]=1[O:17][CH3:18].[Cl:19][C:20]1[CH:21]=[C:22]2[C:26](=[CH:27][CH:28]=1)[NH:25][C:24](=[O:29])[C:23]2=[O:30]>>[Si:8]([O:7][CH2:6][C:5]1[CH:15]=[CH:16][C:2]([C:23]2([OH:30])[C:22]3[C:26](=[CH:27][CH:28]=[C:20]([Cl:19])[CH:21]=3)[NH:25][C:24]2=[O:29])=[C:3]([O:17][CH3:18])[CH:4]=1)([C:11]([CH3:14])([CH3:13])[CH3:12])([CH3:10])[CH3:9]

Participants

3

Reactant 2

HCID 872035-chloro-1H-indole-2,3-dioneHCID 67429327((4-Bromo-3-methoxybenzyl)oxy)(tert-butyl)dimethylsilane

Product 1

HCID 674298243-[4-({[tert-butyl(dimethyl)silyl]oxy}methyl)-2-methoxyphenyl]-5-chloro-3-hydroxy-1,3-dihydro-2H-indol-2-oneYield 21.6%

Procedure

With 6.99 g of the compound obtained in Step 237-2 and 3.21 g of 5-chloroisatin as starting materials, 1.66 g of the title compound (colorless solid) was obtained by a similar method to Step 21-1.

Sources & evidence

ORD record
ord-17731c54dcf24c59adb87a96d5be2d94
Source dataset
uspto-grants-2011_10
Patent number
US08030499B2

Reaction notes

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