1-(diphenylmethyl)-3-hydroxy-3-(6-hydroxy-1,3-benzodioxol-5-yl)-5-methyl-1,3-dihydro-2H-indol-2-one → 1-(diphenylmethyl)-3-(6-hydroxy-1,3-benzodioxol-5-yl)-5-methyl-1,3-dihydro-2H-indol-2-one

HRID 545763Notes

Reaction equation

HRID 545763 reaction equation
C1(CCN2C3C(=CC=CC=3)C(O)(C3C(O)=CC4OCOC=4C=3)C2=O)CC1.[C:27]1([CH:33]([C:56]2[CH:61]=[CH:60][CH:59]=[CH:58][CH:57]=2)[N:34]2[C:42]3[C:37](=[CH:38][C:39]([CH3:43])=[CH:40][CH:41]=3)[C:36](O)([C:44]3[C:52]([OH:53])=[CH:51][C:47]4[O:48][CH2:49][O:50][C:46]=4[CH:45]=3)[C:35]2=[O:55])[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1>>[C:56]1([CH:33]([C:27]2[CH:28]=[CH:29][CH:30]=[CH:31][CH:32]=2)[N:34]2[C:42]3[C:37](=[CH:38][C:39]([CH3:43])=[CH:40][CH:41]=3)[CH:36]([C:44]3[C:52]([OH:53])=[CH:51][C:47]4[O:48][CH2:49][O:50][C:46]=4[CH:45]=3)[C:35]2=[O:55])[CH:57]=[CH:58][CH:59]=[CH:60][CH:61]=1

Participants

3

Reactant 2

HCID 588725111-(diphenylmethyl)-3-hydroxy-3-(6-hydroxy-1,3-benzodioxol-5-yl)-5-methyl-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 120042731-(diphenylmethyl)-3-(6-hydroxy-1,3-benzodioxol-5-yl)-5-methyl-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 1-(diphenylmethyl)-3-hydroxy-3-(6-hydroxy-1,3-benzodioxol-5-yl)-5-methyl-1,3-dihydro-2H-indol-2-one, the title compound was obtained (84%) as a colorless solid: 1H NMR (300 MHz, CDCl3) δ 7.37-7.25 (m, 9H), 7.22-7.17 (m, 2H), 7.10 (s, 1H), 6.91 (s, 1H), 6.86 (d, 1H), 6.63 (s, 1H), 6.40 (s, 1H), 6.38 (d, 1H), 5.88 (ABq, 2H), 5.07 (s, 1H), 2.23 (s, 3H); MS (ES+) m/z 450.3 (M+1).

Sources & evidence

ORD record
ord-b4845d317b6b442b87e4104a8346aff9
Source dataset
uspto-grants-2011_05
Patent number
US07935721B2

Reaction notes

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