4,7-dichloro-3-(6-hydroxy-1,3-benzodioxol-5-yl)-3-(hydroxymethyl)-1-pentyl-1,3-dihydro-2H-indol-2-one → HCID 59263539, compound

HRID 645175Notes

Reaction equation

HRID 645175 reaction equation
[CH3:1][O:2][C:3](=[O:25])[CH2:4][N:5]1[C:13]2[C:8](=[CH:9][CH:10]=[CH:11][CH:12]=2)[C:7]([C:16]2[CH:21]=[CH:20][C:19]([Cl:22])=[CH:18][C:17]=2O)([CH2:14][OH:15])[C:6]1=[O:24].ClC1C=CC(Cl)=C2C=1C(C1C(O)=CC3OCOC=3C=1)(CO)C(=O)N2CCCCC>>[CH3:1][O:2][C:3](=[O:25])[CH2:4][N:5]1[C:13]2[C:8](=[CH:9][CH:10]=[CH:11][CH:12]=2)[C:7]2([C:16]3[CH:17]=[CH:18][C:19]([Cl:22])=[CH:20][C:21]=3[O:15][CH2:14]2)[C:6]1=[O:24]

Participants

3

Reactant 2

HCID 588724744,7-dichloro-3-(6-hydroxy-1,3-benzodioxol-5-yl)-3-(hydroxymethyl)-1-pentyl-1,3-dihydro-2H-indol-2-oneHCID 58872483HCID 58872483, compound

Product 1

HCID 59263539HCID 59263539, compoundYield 74%

Procedure

Following the procedure as described in EXAMPLE 1.22, and making non-critical variations using methyl[3-(4-chloro-2-hydroxyphenyl)-3-(hydroxymethyl)-2-oxo-2,3-dihydro-1H-indol-1-yl]acetate to replace 4,7-dichloro-3-(6-hydroxy-1,3-benzodioxol-5-yl)-3-(hydroxymethyl)-1-pentyl-1,3-dihydro-2H-indol-2-one, the title compound was obtained in 74% yield as a colorless solid: 1H NMR (300 MHz, CDCl3) δ 7.29 (dt, 1H), 7.14 (dd, 1H), 7.06 (t, 1H), 6.95 (d, 1H), 6.81-6.74 (m, 3H), 5.03 (d, 1H), 4.74 (d, 1H), 4.65 (d, 1H), 4.44 (d, 1H), 3.75 (s, 3H); MS (ES+) m/z 344.5 (M+1), 346.5 (M+1).

Sources & evidence

ORD record
ord-afe1b6bae94f48ff9c3f1c80a3b65a2f
Source dataset
uspto-grants-2010_04
Patent number
US07700641B2

Reaction notes

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