Sesamol → ethyl [4-bromo-3-(4,5-difluoro-2-hydroxyphenyl)-3-hydroxy-2-oxo-2,3-dihydro-1H-indol-1-yl]acetate

HRID 425504Notes

Reaction equation

C1(CCN2C3C(=CC=CC=3)C(=O)C2=O)CC1.[Br:17][C:18]1[CH:26]=[CH:25][CH:24]=[C:23]2[C:19]=1[C:20](=[O:34])[C:21](=[O:33])[N:22]2[CH2:27][C:28]([O:30][CH2:31][CH3:32])=[O:29].O1C2C=CC(O)=CC=2OC1.[F:45][C:46]1[CH:47]=[C:48]([OH:53])[CH:49]=[CH:50][C:51]=1[F:52]>>[Br:17][C:18]1[CH:26]=[CH:25][CH:24]=[C:23]2[C:19]=1[C:20]([C:49]1[CH:50]=[C:51]([F:52])[C:46]([F:45])=[CH:47][C:48]=1[OH:53])([OH:34])[C:21](=[O:33])[N:22]2[CH2:27][C:28]([O:30][CH2:31][CH3:32])=[O:29]

Participants

Reactant 4

HCID 68289Sesamol

HCID 759273,4-Difluorophenol

HCID 28492473ethyl (4-bromo-2,3-dioxo-2,3-dihydro-1H-indol-1-yl)acetate

HCID 655965701-(2-cyclopropylethyl)-1H-indole-2,3-dione

Product 1

HCID 58872544ethyl [4-bromo-3-(4,5-difluoro-2-hydroxyphenyl)-3-hydroxy-2-oxo-2,3-dihydro-1H-indol-1-yl]acetate

Procedure

Following the procedure as described in PREPARATION 2B, and making non-critical variations to replace 1-(2-cyclopropylethyl)-1H-indole-2,3-dione with ethyl (4-bromo-2,3-dioxo-2,3-dihydro-1H-indol-1-yl)acetate and 1,3-benzodioxol-5-ol with 3,4-difluorophenol, the title compound was obtained as a white solid (42%); MS (ES+) m/z 424 (M−17), 426 (M−17), 464 (M+23), 466 (M+23).

Sources & evidence

ORD record: ord-0a04e72a76fc4521b6812616df9f8916
Source dataset: uspto-grants-2012_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08106087B2

Reaction notes

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