4-bromo-3-hydroxy-3-(6-hydroxy-2,3-dihydro-1-benzofuran-5-yl)-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 545795Notes

Reaction equation

HRID 545795 reaction equation
C1(CCN2C3C(=CC=CC=3)C(O)(C3C(O)=CC4OCOC=4C=3)C2=O)CC1.[Br:27][C:28]1[CH:36]=[CH:35][CH:34]=[C:33]2[C:29]=1[C:30](O)([C:38]1[C:39]([OH:47])=[CH:40][C:41]3[O:45][CH2:44][CH2:43][C:42]=3[CH:46]=1)[C:31](=[O:37])[NH:32]2>>[Br:27][C:28]1[CH:36]=[CH:35][CH:34]=[C:33]2[C:29]=1[CH:30]([C:38]1[C:39]([OH:47])=[CH:40][C:41]3[O:45][CH2:44][CH2:43][C:42]=3[CH:46]=1)[C:31](=[O:37])[NH:32]2

Participants

3

Reactant 2

HCID 588724674-bromo-3-hydroxy-3-(6-hydroxy-2,3-dihydro-1-benzofuran-5-yl)-1,3-dihydro-2H-indol-2-oneHCID 588725381-(2-cyclopropylethyl)-3-hydroxy-3-(6-hydroxy-1,3-benzodioxol-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 2C, and making non-critical variations to replace 1-(2-cyclopropylethyl)-3-hydroxy-3-(6-hydroxy-1,3-benzodioxol-5-yl)-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 white solid: MS (ES+) m/z 346.5 (M+1), 348.5 (M+1).

Sources & evidence

ORD record
ord-01fedb4c320949cb8e956a733b64b109
Source dataset
uspto-grants-2011_05
Patent number
US07935721B2

Reaction notes

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