3-(Benzo[d][1,3]dioxol-5-yl)-3-hydroxy-1-pentylindolin-2-one → 3-(1,3-benzodioxol-5-yl)-1-pentyl-1,3-dihydro-2H-indol-2-one

HRID 645012Notes

Reaction equation

HRID 645012 reaction equation
[CH:1]1([CH2:4][CH2:5][N:6]2[C:14]3[C:9](=[CH:10][CH:11]=[CH:12][CH:13]=3)[C:8](O)([C:15]3[C:23](O)=[CH:22][C:18]4[O:19][CH2:20][O:21][C:17]=4[CH:16]=3)[C:7]2=[O:26])[CH2:3][CH2:2]1.O1C2C=CC(C3(O)C4C(=CC=CC=4)N(CCCCC)C3=O)=CC=2OC1>>[O:19]1[C:18]2[CH:22]=[CH:23][C:15]([CH:8]3[C:9]4[C:14](=[CH:13][CH:12]=[CH:11][CH:10]=4)[N:6]([CH2:5][CH2:4][CH2:1][CH2:2][CH3:3])[C:7]3=[O:26])=[CH:16][C:17]=2[O:21][CH2:20]1

Participants

3

Reactant 2

HCID 120043373-(Benzo[d][1,3]dioxol-5-yl)-3-hydroxy-1-pentylindolin-2-oneHCID 588725381-(2-cyclopropylethyl)-3-hydroxy-3-(6-hydroxy-1,3-benzodioxol-5-yl)-1,3-dihydro-2H-indol-2-one

Product 1

HCID 545816533-(1,3-benzodioxol-5-yl)-1-pentyl-1,3-dihydro-2H-indol-2-one

Procedure

Following the procedure as described in PREPARATION 2C, and making non-critical variations to replace 1-(2-cyclopropylethyl)-3-hydroxy-3-(6-hydroxy-1,3-benzodioxol-5-yl)-1,3-dihydro-2H-indol-2-one with 3-(1,3-benzodioxol-5-yl)-3-hydroxy-1-pentyl-1,3-dihydro-2H-indol-2-one, the title compound was obtained (90%) as an oil: 1H NMR (300 MHz, CDCl3) δ 7.30 (td, 1H), 7.14 (d, 1H), 7.03 (td, 1H), 6.89 (d, 1H), 6.75 (d, 1H), 6.67 (dd, 1H), 6.57 (d, 1H), 5.90 (s, 2H), 4.50 (s, 1H), 3.81-3.62 (m, 2H), 1.76-1.62 (m, 2H), 1.41-1.28 (m, 4H), 0.88 (t, 3H); 13C NMR (75 MHz, CDCl3) 6176.8, 148.1, 147.2, 143.5, 130.0, 129.4, 128.4, 125.1, 122.9, 122.0, 108.7, 108.6, 101.1, 51.9, 40.4, 29.0, 27.1, 22.3, 14.0.

Sources & evidence

ORD record
ord-0dae5a1a9f8043dca6b0294c5fa20f23
Source dataset
uspto-grants-2010_04
Patent number
US07700641B2

Reaction notes

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