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

HRID 645047Notes

Reaction equation

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

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-fa67824fa1e34842bb653842120e2b6c
Source dataset: uspto-grants-2010_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07700641B2

Reaction notes

Loading…