ethyl [4-bromo-3-hydroxy-3-(6-hydroxy-2,3-dihydro-1-benzofuran-5-yl)-2-oxo-2,3-dihydro-1H-indol-1-yl]acetate → ethyl [4-bromo-3-(6-hydroxy-2,3-dihydro-1-benzofuran-5-yl)-2-oxo-2,3-dihydro-1H-indol-1-yl]acetate

HRID 645098Notes

Reaction equation

HRID 645098 reaction equation
C1(CCN2C3C(=CC=CC=3)C(O)(C3C(O)=CC4OCOC=4C=3)C2=O)CC1.[CH2:27]([O:29][C:30](=[O:54])[CH2:31][N:32]1[C:40]2[C:35](=[C:36]([Br:41])[CH:37]=[CH:38][CH:39]=2)[C:34](O)([C:42]2[C:43]([OH:51])=[CH:44][C:45]3[O:49][CH2:48][CH2:47][C:46]=3[CH:50]=2)[C:33]1=[O:53])[CH3:28]>>[CH2:27]([O:29][C:30](=[O:54])[CH2:31][N:32]1[C:40]2[C:35](=[C:36]([Br:41])[CH:37]=[CH:38][CH:39]=2)[CH:34]([C:42]2[C:43]([OH:51])=[CH:44][C:45]3[O:49][CH2:48][CH2:47][C:46]=3[CH:50]=2)[C:33]1=[O:53])[CH3:28]

Participants

3

Reactant 2

HCID 58872433ethyl [4-bromo-3-hydroxy-3-(6-hydroxy-2,3-dihydro-1-benzofuran-5-yl)-2-oxo-2,3-dihydro-1H-indol-1-yl]acetateHCID 588725381-(2-cyclopropylethyl)-3-hydroxy-3-(6-hydroxy-1,3-benzodioxol-5-yl)-1,3-dihydro-2H-indol-2-one

Product 1

HCID 58872559ethyl [4-bromo-3-(6-hydroxy-2,3-dihydro-1-benzofuran-5-yl)-2-oxo-2,3-dihydro-1H-indol-1-yl]acetate

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 ethyl[4-bromo-3-hydroxy-3-(6-hydroxy-2,3-dihydro-1-benzofuran-5-yl)-2-oxo-2,3-dihydro-1H-indol-1-yl]acetate, the title compound was obtained (81%) as a white solid: 1H NMR (CDCl3, 300 MHz) δ 7.31-7.19 (m, 3H), 6.75 (d, 1H), 6.50-6.45 (m, 1H), 5.08 (s, 1H), 5.09-4.36 (m, 4H), 4.20 (q, 2H), 3.14-2.90 (m, 2H), 1.23 (t, 3H); MS (ES+) m/z 433.3 (M+1).

Sources & evidence

ORD record
ord-d3c7c8f7138d431c932e9c233cb4aff5
Source dataset
uspto-grants-2010_04
Patent number
US07700641B2

Reaction notes

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