3-(5-bromo-2-hydroxyphenyl)-3-hydroxy-1-pentyl-1,3-dihydro-2H-indol-2-one → ethyl [3-(3-hydroxy-5,6,7,8-tetrahydronaphthalen-2-yl)-2-oxo-2,3-dihydro-1H-indol-1-yl]acetate

HRID 1259595Notes

Reaction equation

HRID 1259595 reaction equation
BrC1C=CC(O)=C(C2(O)C3C(=CC=CC=3)N(CCCCC)C2=O)C=1.O[C:26]1([C:42]2[C:51]([OH:52])=[CH:50][C:49]3[CH2:48][CH2:47][CH2:46][CH2:45][C:44]=3[CH:43]=2)[C:34]2[C:29](=[CH:30][CH:31]=[CH:32][CH:33]=2)[N:28]([CH2:35][C:36]([O:38][CH2:39][CH3:40])=[O:37])[C:27]1=[O:41]>>[OH:52][C:51]1[C:42]([CH:26]2[C:34]3[C:29](=[CH:30][CH:31]=[CH:32][CH:33]=3)[N:28]([CH2:35][C:36]([O:38][CH2:39][CH3:40])=[O:37])[C:27]2=[O:41])=[CH:43][C:44]2[CH2:45][CH2:46][CH2:47][CH2:48][C:49]=2[CH:50]=1

Participants

3

Reactant 2

HCID 588724783-(5-bromo-2-hydroxyphenyl)-3-hydroxy-1-pentyl-1,3-dihydro-2H-indol-2-oneHCID 58872545ethyl [3-hydroxy-3-(3-hydroxy-5,6,7,8-tetrahydronaphthalen-2-yl)-2-oxo-2,3-dihydro-1H-indol-1-yl]acetate

Product 1

HCID 58872466ethyl [3-(3-hydroxy-5,6,7,8-tetrahydronaphthalen-2-yl)-2-oxo-2,3-dihydro-1H-indol-1-yl]acetate

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 ethyl [3-hydroxy-3-(3-hydroxy-5,6,7,8-tetrahydronaphthalen-2-yl)-2-oxo-2,3-dihydro-1H-indol-1-yl]acetate, the title compound was obtained: 1H NMR (300 MHz, CDCl3) δ 7.42-7.32 (m, 2H), 7.20 (t, 1H), 6.84 (d, 1H), 6.78 (s, 1H), 6.61 (s, 1H), 5.12 (s, 1H), 4.47 (ABq, 2H), 4.21 (q, 2H), 2.76-2.44 (m, 4H), 1.78-1.64 (m, 4H), 1.24 (t, 3H); MS (ES+) m/z 366 (M+1).

Sources & evidence

ORD record
ord-ec78a166a5814af19f082c8e4805c04b
Source dataset
uspto-grants-2013_06
Patent number
US08466188B2

Reaction notes

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