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

HRID 545776Notes

Reaction equation

HRID 545776 reaction equation
BrC1C=CC=C2C=1C(=O)C(=O)N2CCCCC.[Cl:18][C:19]1[CH:20]=[C:21]2[C:25](=[CH:26][CH:27]=1)[N:24]([CH2:28][C:29]([O:31][CH2:32][CH3:33])=[O:30])[C:23](=[O:34])[C:22]2=[O:35].O1C2C=CC(O)=CC=2OC1.[O:46]1[C:50]2[CH:51]=[C:52]([OH:55])[CH:53]=[CH:54][C:49]=2[CH2:48][CH2:47]1>>[Cl:18][C:19]1[CH:20]=[C:21]2[C:25](=[CH:26][CH:27]=1)[N:24]([CH2:28][C:29]([O:31][CH2:32][CH3:33])=[O:30])[C:23](=[O:34])[C:22]2([OH:35])[C:53]1[C:52]([OH:55])=[CH:51][C:50]2[O:46][CH2:47][CH2:48][C:49]=2[CH:54]=1

Participants

5

Reactant 4

HCID 68289SesamolHCID 122365402,3-Dihydro-1-benzofuran-6-olHCID 284924584-bromo-1-pentyl-1H-indole-2,3-dioneHCID 28492634Ethyl 2-(5-chloro-2,3-dioxoindolin-1-yl)acetate

Product 1

HCID 58872441ethyl [5-chloro-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 1C, and making non-critical variations to replace 4-bromo-1-pentyl-1H-indole-2,3-dione with ethyl (5-chloro-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 (85%) as a white solid: 1H NMR (300 MHz, CDCl3) δ 8.70 (br, 1H), 7.31-7.24 (m, 2H), 6.92 (d, 1H), 6.68 (s, 1H), 6.46 (s, 1H), 4.53-4.46 (m, 2H), 5.09-4.40 (d, 2H), 4.18 (q, 2H), 3.08-2.88 (m, 2H), 1.23 (t, 3H); MS (ES+) m/z 387.8 (M−17).

Sources & evidence

ORD record
ord-8b4f1b71475244e5baa2e1af478ee10f
Source dataset
uspto-grants-2011_05
Patent number
US07935721B2

Reaction notes

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