Sesamol → 4-bromo-3-hydroxy-3-(6-hydroxy-2,3-dihydro-1-benzofuran-5-yl)-1,3-dihydro-2H-indol-2-one

HRID 425576Notes

Reaction equation

O1C2C=CC(O)=CC=2OC1.[O:11]1[C:15]2[CH:16]=[C:17]([OH:20])[CH:18]=[CH:19][C:14]=2[CH2:13][CH2:12]1.C1(CCN2C3C(=CC=CC=3)C(=O)C2=O)CC1.[Br:37][C:38]1[CH:46]=[CH:45][CH:44]=[C:43]2[C:39]=1[C:40](=[O:48])[C:41](=[O:47])[NH:42]2>>[Br:37][C:38]1[CH:46]=[CH:45][CH:44]=[C:43]2[C:39]=1[C:40]([OH:48])([C:18]1[C:17]([OH:20])=[CH:16][C:15]3[O:11][CH2:12][CH2:13][C:14]=3[CH:19]=1)[C:41](=[O:47])[NH:42]2

Participants

Reactant 4

HCID 68289Sesamol

HCID 45000124-Bromoisatin

HCID 122365402,3-Dihydro-1-benzofuran-6-ol

HCID 655965701-(2-cyclopropylethyl)-1H-indole-2,3-dione

Product 1

HCID 588724674-bromo-3-hydroxy-3-(6-hydroxy-2,3-dihydro-1-benzofuran-5-yl)-1,3-dihydro-2H-indol-2-one

Procedure

Following the procedure as described in PREPARATION 2B, and making non-critical variations to replace 1,3-benzodioxol-5-ol with 2,3-dihydrobenzofuran-6-ol and 1-(2-cyclopropylethyl)-1H-indole-2,3-dione with 4-bromo-1H-indole-2,3-dione, the title compound was obtained (78%) as a white solid: 1H NMR (300 MHz, DMSO-d6) δ 10.36 (s, 1H), 9.15 (s, 1H), 7.49 (1H), 7.04 (t, 1H), 6.89 (d, 1H), 6.74 (d, 1H), 6.35 (br, 1H), 5.90 (s, 1H), 4.45 (t, 2H), 3.05 (t, 2H); 13C NMR (75 MHz, DMSO-d6) δ 178.4, 160.2, 154.0, 145.7, 131.6, 130.7, 125.5, 125.4, 118.9, 117.7, 116.1, 108.8, 96.8, 76.9, 71.8, 29.1; MS (ES−) m/z 344.4 (M−17), 360.4 (M−1).

Sources & evidence

ORD record: ord-fd27400671824c75b9936d1da81aa919
Source dataset: uspto-grants-2012_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08106087B2

Reaction notes

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