4,7-dichloro-3-(6-hydroxy-1,3-benzodioxol-5-yl)-3-(hydroxymethyl)-1-pentyl-1,3-dihydro-2H-indol-2-one → ethyl(5'-chloro-2'-oxo-5,6-dihydrospiro[benzo[1,2-b:5,4-b']difuran-3,3'-indol]-1'(2'H)-yl)acetate

HRID 645173Notes

Reaction equation

HRID 645173 reaction equation
[CH2:1]([O:3][C:4](=[O:29])[CH2:5][N:6]1[C:14]2[C:9](=[CH:10][C:11]([Cl:15])=[CH:12][CH:13]=2)[C:8]([C:18]2[C:19](O)=[CH:20][C:21]3[O:25][CH2:24][CH2:23][C:22]=3[CH:26]=2)([CH2:16][OH:17])[C:7]1=[O:28])[CH3:2].ClC1C=CC(Cl)=C2C=1C(C1C(O)=CC3OCOC=3C=1)(CO)C(=O)N2CCCCC>>[CH2:1]([O:3][C:4](=[O:29])[CH2:5][N:6]1[C:14]2[C:9](=[CH:10][C:11]([Cl:15])=[CH:12][CH:13]=2)[C:8]2([CH2:16][O:17][C:19]3[CH:20]=[C:21]4[C:22](=[CH:26][C:18]2=3)[CH2:23][CH2:24][O:25]4)[C:7]1=[O:28])[CH3:2]

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 58872495ethyl [5-chloro-3-(6-hydroxy-2,3-dihydro-1-benzofuran-5-yl)-3-(hydroxymethyl)-2-oxo-2,3-dihydro-1H-indol-1-yl]acetate

Product 1

HCID 59263353ethyl(5'-chloro-2'-oxo-5,6-dihydrospiro[benzo[1,2-b:5,4-b']difuran-3,3'-indol]-1'(2'H)-yl)acetateYield 90%

Procedure

Following the procedure as described in EXAMPLE 1.22, and making non-critical variations using ethyl[5-chloro-3-(6-hydroxy-2,3-dihydro-1-benzofuran-5-yl)-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 90% yield as a colorless solid: MS (ES+) m/z 400.8 (M+1).

Sources & evidence

ORD record
ord-5b4160e0fad548a3b8af4c0f1455cc44
Source dataset
uspto-grants-2010_04
Patent number
US07700641B2

Reaction notes

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