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 545846Notes

Reaction equation

HRID 545846 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[N:7]([CH2:11][C:12]([O:14][CH2:15][CH3:16])=[O:13])[C:6](=[O:17])[C:5]2([C:20]1[C:21]([OH:29])=[CH:22][C:23]2[O:27][CH2:26][CH2:25][C:24]=2[CH:28]=1)[CH2:18]O.ClC1C=CC(Cl)=C2C=1C(C1C(O)=CC3OCOC=3C=1)(CO)C(=O)N2CCCCC>>[Cl:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[N:7]([CH2:11][C:12]([O:14][CH2:15][CH3:16])=[O:13])[C:6](=[O:17])[C:5]12[CH2:18][O:29][C:21]2[CH:22]=[C:23]3[C:24](=[CH:28][C:20]1=2)[CH2:25][CH2:26][O:27]3

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-b45899054e214b76a1ef3d95c3fb33ca
Source dataset
uspto-grants-2011_05
Patent number
US07935721B2

Reaction notes

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