3-(5-bromo-2-hydroxy-4-methoxyphenyl)-3-hydroxy-1-pentyl-1,3-dihydro-2H-indol-2-one → 3-(2-hydroxy-4-methoxyphenyl)-1-pentyl-1,3-dihydro-2H-indol-2-one

HRID 425495Notes

Reaction equation

HRID 425495 reaction equation
BrC1C=CC(O)=C(C2(O)C3C(=CC=CC=3)N(CCCCC)C2=O)C=1.Br[C:26]1[C:27]([O:49][CH3:50])=[CH:28][C:29]([OH:48])=[C:30]([C:32]2(O)[C:40]3[C:35](=[CH:36][CH:37]=[CH:38][CH:39]=3)[N:34]([CH2:41][CH2:42][CH2:43][CH2:44][CH3:45])[C:33]2=[O:46])[CH:31]=1>>[OH:48][C:29]1[CH:28]=[C:27]([O:49][CH3:50])[CH:26]=[CH:31][C:30]=1[CH:32]1[C:40]2[C:35](=[CH:36][CH:37]=[CH:38][CH:39]=2)[N:34]([CH2:41][CH2:42][CH2:43][CH2:44][CH3:45])[C:33]1=[O:46]

Participants

3

Reactant 2

HCID 120043323-(5-bromo-2-hydroxy-4-methoxyphenyl)-3-hydroxy-1-pentyl-1,3-dihydro-2H-indol-2-oneHCID 588724783-(5-bromo-2-hydroxyphenyl)-3-hydroxy-1-pentyl-1,3-dihydro-2H-indol-2-one

Product 1

HCID 588725483-(2-hydroxy-4-methoxyphenyl)-1-pentyl-1,3-dihydro-2H-indol-2-one

Procedure

Following the procedure as described in PREPARATION 15B, and making non-critical variations to replace 3-(5-bromo-2-hydroxyphenyl)-3-hydroxy-1-pentyl-1,3-dihydro-2H-indol-2-one with 3-(5-bromo-2-hydroxy-4-methoxyphenyl)-3-hydroxy-1-pentyl-1,3-dihydro-2H-indol-2-one, the title compound was obtained (83%): 1H NMR (300 MHz, CDCl3) δ 9.78-9.20 (br, 1H), 7.43-7.31 (m, 2H), 7.19 (t, 1H), 6.97 (d, 1H), 6.79 (d, 1H), 6.70-6.64 (m, 1H), 6.38 (dd, 1H), 5.02 (s, 1H), 3.77 (s, 3H), 3.70 (t, 2H), 1.75-1.63 (m, 2H), 1.40-1.25 (m, 4H), 0.87 (t, 3H); MS (ES+) m/z 326 (M+1).

Sources & evidence

ORD record
ord-e4fc5831b567478382f3f768ea9e30d9
Source dataset
uspto-grants-2012_01
Patent number
US08106087B2

Reaction notes

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