Isatin → 5-Chloro-3-[2-(2,2-difluoroethoxy)phenyl]-6-fluoro-3-hydroxy-1,3-dihydroindol-2-one

HRID 1035835Notes

Reaction equation

[Cl:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][C:10]=1[F:11])[NH:7][C:6](=[O:12])[C:5]2=[O:13].N1C2C(=CC=CC=2)C(=O)C1=O.[F:25][CH:26]([F:36])[CH2:27][O:28][C:29]1[CH:34]=[CH:33][CH:32]=[CH:31][C:30]=1I>>[Cl:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][C:10]=1[F:11])[NH:7][C:6](=[O:12])[C:5]2([C:30]1[CH:31]=[CH:32][CH:33]=[CH:34][C:29]=1[O:28][CH2:27][CH:26]([F:25])[F:36])[OH:13]

Participants

Reactant 3

HCID 7054Isatin

HCID 167818735-Chloro-6-fluoroindoline-2,3-dione

HCID 614001452,2-Difluoroethoxyiodobenzene

Product 1

HCID 867254505-Chloro-3-[2-(2,2-difluoroethoxy)phenyl]-6-fluoro-3-hydroxy-1,3-dihydroindol-2-one

Procedure

The title compound was prepared in analogy to example a.1 using 5-chloro-6-fluoro-isatin as isatin II and 2,2-difluoroethoxyiodobenzene (to form the Grignard reagent).

Sources & evidence

ORD record: ord-223f1e7e25094867b41a30c1b9e5f803
Source dataset: uspto-grants-2013_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08546401B2

Reaction notes

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