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 545715Notes

Reaction equation

BrC1C=CC=C2C=1C(=O)C(=O)N2CCCCC.[O:18]=[C:19]1[C:27](=[O:28])[C:26]2[C:21](=[CH:22][CH:23]=[CH:24][CH:25]=2)[N:20]1[CH2:29][C:30]([O:32][CH2:33][CH3:34])=[O:31].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>>[OH:28][C:27]1([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:26]2[C:21](=[CH:22][CH:23]=[CH:24][CH:25]=2)[N:20]([CH2:29][C:30]([O:32][CH2:33][CH3:34])=[O:31])[C:19]1=[O:18]

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-e507459721ce447c83aaaa963510ea7e
Source dataset: uspto-grants-2011_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07935721B2

Reaction notes

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