4-bromo-3-hydroxy-3-(6-hydroxy-1,3-benzodioxol-5-yl)-1-pentyl-1,3-dihydro-2H-indol-2-one → HCID 58872449, compound

HRID 645007Notes

Reaction equation

HRID 645007 reaction equation
BrC1C=CC=C2C=1C(O)(C1C(O)=CC3OCOC=3C=1)C(=O)N2CCCCC.[CH2:28]([O:35][CH2:36][CH2:37][CH2:38][N:39]1[C:47]2[C:42](=[CH:43][CH:44]=[CH:45][CH:46]=2)[C:41](O)([C:48]2[C:56]([OH:57])=[CH:55][C:51]3[O:52][CH2:53][O:54][C:50]=3[CH:49]=2)[C:40]1=[O:59])[C:29]1[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=1>>[CH2:28]([O:35][CH2:36][CH2:37][CH2:38][N:39]1[C:47]2[C:42](=[CH:43][CH:44]=[CH:45][CH:46]=2)[CH:41]([C:48]2[C:56]([OH:57])=[CH:55][C:51]3[O:52][CH2:53][O:54][C:50]=3[CH:49]=2)[C:40]1=[O:59])[C:29]1[CH:30]=[CH:31][CH:32]=[CH:33][CH:34]=1

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 58872451HCID 58872451, compound

Product 1

HCID 58872449HCID 58872449, compound

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 1-[3-(benzyloxy)propyl]-3-hydroxy-3-(6-hydroxy-1,3-benzodioxol-5-yl)-1,3-dihydro-2H-indol-2-one, the title compound was obtained (92%): 1H NMR (300 MHz, CDCl3) δ7.42-6.95 (m, 9H), 6.56 (s, 1H), 6.24 (s, 1H), 5.86 (ABq, 1H), 5.81(ABq, 1H), 4.99 (s, 1H), 4.42 (s, 2H), 3.91-3.76 (m, 2H), 3.46 (t, 2H), 2.03-1.93 (m, 2H); MS (ES+) m/z 418.3 (M+1).

Sources & evidence

ORD record
ord-312da45acecf4c4988c7f1c0fd44b097
Source dataset
uspto-grants-2010_04
Patent number
US07700641B2

Reaction notes

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