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

HRID 425554Notes

Reaction equation

HRID 425554 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.[O:45]1[C:49]2[CH:50]=[C:51]([OH:54])[CH:52]=[CH:53][C:48]=2[CH2:47][CH2:46]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:51]([OH:54])=[CH:50][C:49]3[O:45][CH2:46][CH2:47][C:48]=3[CH:53]=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 122365402,3-Dihydro-1-benzofuran-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 58872433ethyl [4-bromo-3-hydroxy-3-(6-hydroxy-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 2,3-dihydrobenzofuran-6-ol, the title compound was obtained (68%) as a white solid: 1H NMR (300 MHz, CDCl3) δ 8.66 (br, 1H), 7.31-7.19 (m, 3H), 6.73 (dd, 1H), 6.49-6.45 (m, 1H), 5.09-4.36 (m, 4H), 4.20 (q, 2H), 3.14-2.90 (m, 2H), 1.23 (t, 3H); MS (ES+) m/z 432.2 (M−17).

Sources & evidence

ORD record
ord-78edb2eb2ff042a48c42a10bd0557ac8
Source dataset
uspto-grants-2012_01
Patent number
US08106087B2

Reaction notes

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