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

HRID 645040Notes

Reaction equation

BrC1C=CC=C2C=1C(=O)C(=O)N2CCCCC.[CH2:18]([O:20][C:21](=[O:34])[CH2:22][N:23]1[C:31]2[C:26](=[CH:27][CH:28]=[CH:29][CH:30]=2)[C:25](=[O:32])[C:24]1=[O:33])[CH3:19].O1C2C=CC(O)=CC=2OC1.[CH2:45]1[C:53]2[C:48](=[CH:49][C:50]([OH:54])=[CH:51][CH:52]=2)[CH2:47][CH2:46]1>>[CH2:18]([O:20][C:21](=[O:34])[CH2:22][N:23]1[C:31]2[C:26](=[CH:27][CH:28]=[CH:29][CH:30]=2)[C:25]([OH:32])([C:51]2[CH:52]=[C:53]3[C:48](=[CH:49][C:50]=2[OH:54])[CH2:47][CH2:46][CH2:45]3)[C:24]1=[O:33])[CH3:19]

Participants

Reactant 4

HCID 151185-Indanol

HCID 38750Ethyl isatin-N-acetate

HCID 68289Sesamol

HCID 284924584-bromo-1-pentyl-1H-indole-2,3-dione

Product 1

HCID 58872494ethyl [3-hydroxy-3-(6-hydroxy-2,3-dihydro-1H-inden-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(2,3-dioxo-2,3-dihydro-1H-indol-1-yl)acetate, and 1,3-benzodioxol-5-ol with 5-indanol, the title compound was obtained (84%): 1H NMR (300 MHz, CDCl3) δ 8.76 (s, 1H), 7.55 (d, 1H), 7.38 (td, 1H), 7.20 (t, 1H), 6.9 (s, 1H), 6.80 (d, 1H), 6.65 (s, 1H), 4.45 (ABq, 2H), 4.32-4.25 (br, 1H), 4.20 (q, 2H), 2.83 (t, 2H), 2.74-2.65 (m, 2H), 2.06-1.94 (m, 2H), 1.27 (t, 3H); MS (ES+) m/z 350 (M−17), 390 (M+23).

Sources & evidence

ORD record: ord-5f6824a9225a44a993a0cac2f48315fb
Source dataset: uspto-grants-2010_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07700641B2

Reaction notes

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