3-(4-chloro-5-fluoro-2-hydroxyphenyl)-3-(hydroxymethyl)-1-pentyl-1,3-dihydro-2H-indol-2-one → 6-chloro-5-fluoro-1'-pentylspiro[1-benzofuran-3,3'-indol]-2'(1'H)-one

HRID 545824Notes

Reaction equation

HRID 545824 reaction equation
[Cl:1][C:2]1[C:7]([F:8])=[CH:6][C:5]([C:9]2([CH2:24][OH:25])[C:17]3[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=3)[N:11]([CH2:18][CH2:19][CH2:20][CH2:21][CH3:22])[C:10]2=[O:23])=[C:4](O)[CH:3]=1.C1(CCN2C3C(=CC=CC=3)C(C3C(O)=CC4OCOC=4C=3)(CO)C2=O)CC1>>[Cl:1][C:2]1[C:7]([F:8])=[CH:6][C:5]2[C:9]3([CH2:24][O:25][C:4]=2[CH:3]=1)[C:17]1[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=1)[N:11]([CH2:18][CH2:19][CH2:20][CH2:21][CH3:22])[C:10]3=[O:23]

Participants

3

Reactant 2

HCID 588725043-(4-chloro-5-fluoro-2-hydroxyphenyl)-3-(hydroxymethyl)-1-pentyl-1,3-dihydro-2H-indol-2-oneHCID 666425671-(2-cyclopropylethyl)-3-(6-hydroxy-1,3-benzodioxol-5-yl)-3-(hydroxymethyl)-1,3-dihydro-2H-indol-2-one

Product 1

HCID 592633386-chloro-5-fluoro-1'-pentylspiro[1-benzofuran-3,3'-indol]-2'(1'H)-oneYield 44%

Procedure

Following the procedure as described in EXAMPLE 1, and making non-critical variations using 3-(4-chloro-5-fluoro-2-hydroxyphenyl)-3-(hydroxymethyl)-1-pentyl-1,3-dihydro-2H-indol-2-one to replace 1-(2-cyclopropylethyl)-3-(6-hydroxy-1,3-benzodioxol-5-yl)-3-(hydroxymethyl)-1,3-dihydro-2H-indol-2-one, the title compound was obtained in 44% yield: 1H NMR (300 MHz, CDCl3) δ 7.34 (td, 1H), 7.14 (dd, 1H), 7.06 (td, 1H), 6.98 (d, 1H), 6.93 (d, 1H), 6.50 (d, 1H), 4.96 (d, 1H), 4.70 (d, 1H), 3.87-3.63 (m, 2H), 1.81-1.65 (m, 2H), 1.47-1.29 (m, 4H), 0.91 (t, 3H); 13C NMR (75 MHz, CDCl3) δ 176.2, 156.9, 154.8, 151.6, 142.5, 131.5, 129.4, 128.6, 123.7, 121.7, 121.9, 111.2, 108.9, 80.6, 57.9, 40.5, 29.0, 27.1, 22.3, 14.0; MS (ES+) m/z 360 (M+1).

Sources & evidence

ORD record
ord-e9da51df4f1847e8b51d5842b9c7fa42
Source dataset
uspto-grants-2011_05
Patent number
US07935721B2

Reaction notes

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