4-bromo-3-hydroxy-3-(6-hydroxy-1,3-benzodioxol-5-yl)-1-pentyl-1,3-dihydro-2H-indol-2-one → 4-bromo-3-(6-hydroxy-2,3-dihydro-1-benzofuran-5-yl)-1,3-dihydro-2H-indol-2-one

HRID 545752Notes

Reaction equation

HRID 545752 reaction equation
BrC1C=CC=C2C=1C(O)(C1C(O)=CC3OCOC=3C=1)C(=O)N2CCCCC.[Br:28][C:29]1[CH:37]=[CH:36][CH:35]=[C:34]2[C:30]=1[C:31](O)([C:39]1[C:40]([OH:48])=[CH:41][C:42]3[O:46][CH2:45][CH2:44][C:43]=3[CH:47]=1)[C:32](=[O:38])[NH:33]2>>[Br:28][C:29]1[CH:37]=[CH:36][CH:35]=[C:34]2[C:30]=1[CH:31]([C:39]1[C:40]([OH:48])=[CH:41][C:42]3[O:46][CH2:45][CH2:44][C:43]=3[CH:47]=1)[C:32](=[O:38])[NH:33]2

Participants

3

Reactant 2

HCID 120044004-bromo-3-hydroxy-3-(6-hydroxy-1,3-benzodioxol-5-yl)-1-pentyl-1,3-dihydro-2H-indol-2-oneHCID 588724674-bromo-3-hydroxy-3-(6-hydroxy-2,3-dihydro-1-benzofuran-5-yl)-1,3-dihydro-2H-indol-2-one

Product 1

HCID 120044054-bromo-3-(6-hydroxy-2,3-dihydro-1-benzofuran-5-yl)-1,3-dihydro-2H-indol-2-one

Procedure

Following the procedure as described in PREPARATION 1D, and making non-critical variations to replace 4-bromo-3-hydroxy-3-(6-hydroxy-1,3-benzodioxol-5-yl)-1-pentyl-1,3-dihydro-2H-indol-2-one with 4-bromo-3-hydroxy-3-(6-hydroxy-2,3-dihydro-1-benzofuran-5-yl)-1,3-dihydro-2H-indol-2-one, the title compound was obtained (62%) as a solid: MS (ES+) m/z 346.5 (M+1), 348.5 (M+1).

Sources & evidence

ORD record
ord-f1ecc49883d140639eeaec54edc5ebdb
Source dataset
uspto-grants-2011_05
Patent number
US07935721B2

Reaction notes

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