4,7-dichloro-3-(6-hydroxy-1,3-benzodioxol-5-yl)-3-(hydroxymethyl)-1-pentyl-1,3-dihydro-2H-indol-2-one → 6-bromo-1'-pentylspiro[1-benzofuran-3,3'-indol]-2'(1'H)one

HRID 425616Notes

Reaction equation

HRID 425616 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2([CH2:23][OH:24])[C:16]3[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=3)[N:10]([CH2:17][CH2:18][CH2:19][CH2:20][CH3:21])[C:9]2=[O:22])=[C:4](O)[CH:3]=1.ClC1C=CC(Cl)=C2C=1C(C1C(O)=CC3OCOC=3C=1)(CO)C(=O)N2CCCCC>>[Br:1][C:2]1[CH:3]=[CH:4][C:5]2[C:8]3([CH2:23][O:24][C:6]=2[CH:7]=1)[C:16]1[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=1)[N:10]([CH2:17][CH2:18][CH2:19][CH2:20][CH3:21])[C:9]3=[O:22]

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 588725533-(4-bromo-2-hydroxyphenyl)-3-(hydroxymethyl)-1-pentyl-1,3-dihydro-2H-indol-2-one

Product 1

HCID 592634366-bromo-1'-pentylspiro[1-benzofuran-3,3'-indol]-2'(1'H)oneYield 82%

Procedure

Following the procedure as described in EXAMPLE 1.22, and making non-critical variations using 3-(4-bromo-2-hydroxyphenyl)-3-(hydroxymethyl)-1-pentyl-1,3-dihydro-2H-indol-2-one 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 82% yield as a colorless solid: 1H NMR (300 MHz, CDCl3) δ 7.33 (td, 1H), 7.15-7.14 (m, 2H), 7.04 (dd, 1H), 6.96-6.90 (m, 2H), 6.56 (d, 1H), 4.95 (d, 1H), 4.69 (d, 1H), 3.89-3.64 (m, 2H), 1.80-1.68 (m, 2H), 1.43-1.34 (m, 4H), 0.92 (t, 3H); 13C NMR (75 MHz, CDCl3) δ 176.6, 161.6, 142.5, 132.1, 129.1, 128.4, 124.4, 123.9, 123.3, 122.8, 114.1, 108.8, 80.4, 57.6, 40.4, 29.0, 27.1, 22.3, 14.0; MS (ES+) m/z 386.3 (M+1), 388.3 (M+1).

Sources & evidence

ORD record
ord-1cf53f2fa49b476586b6f2fa6111f9a4
Source dataset
uspto-grants-2012_01
Patent number
US08106087B2

Reaction notes

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