Sesamol → ethyl [4-bromo-3-hydroxy-3-(6-hydroxy-2,2-dimethyl-2,3-dihydro-1-benzofuran-5-yl)-2-oxo-2,3-dihydro-1H-indol-1-yl]acetate

HRID 425509Notes

Reaction equation

HRID 425509 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.[CH3:45][C:46]1([CH3:56])[CH2:50][C:49]2[CH:51]=[CH:52][C:53]([OH:55])=[CH:54][C:48]=2[O:47]1>>[Br:17][C:18]1[CH:26]=[CH:25][CH:24]=[C:23]2[C:19]=1[C:20]([OH:34])([C:52]1[C:53]([OH:55])=[CH:54][C:48]3[O:47][C:46]([CH3:56])([CH3:45])[CH2:50][C:49]=3[CH:51]=1)[C:21](=[O:33])[N:22]2[CH2:27][C:28]([O:30][CH2:31][CH3:32])=[O:29]

Participants

5

Reactant 4

HCID 68289SesamolHCID 200372932,2-Dimethyl-2,3-dihydrobenzofuran-6-olHCID 28492473ethyl (4-bromo-2,3-dioxo-2,3-dihydro-1H-indol-1-yl)acetateHCID 655965701-(2-cyclopropylethyl)-1H-indole-2,3-dione

Product 1

HCID 58872452ethyl [4-bromo-3-hydroxy-3-(6-hydroxy-2,2-dimethyl-2,3-dihydro-1-benzofuran-5-yl)-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 2,2-dimethyl-2,3-dihydrobenzofuran-6-ol, the title compound was obtained: MS (ES+) m/z 498.5 (M+23), 500.5 (M+23).

Sources & evidence

ORD record
ord-75fd3969a9ab48b695d24b800d510154
Source dataset
uspto-grants-2012_01
Patent number
US08106087B2

Reaction notes

Loading…