3-((1H-indol-3-yl)methyl)-5-chloro-2-oxo-1-propylindolin-3-yl benzoate → 3-((1-benzoyl-1H-indol-3-yl)methyl)-3-hydroxy-5-methyl-1-propylindolin-2-one

HRID 1523099Notes

Reaction equation

HRID 1523099 reaction equation
C(OC1(CC2C3C(=CC=CC=3)NC=2)C2C(=CC=C(Cl)C=2)N(CCC)C1=O)(=O)C1C=CC=CC=1.C([O:42][CH:43]1[C:51]2[C:46](=[CH:47][CH:48]=[C:49]([CH3:52])[CH:50]=2)[N:45]([CH2:53][CH2:54][CH3:55])[C:44]1=[O:56])(=O)C1C=CC=CC=1.C(O[CH2:66][C:67]1[C:75]2[C:70](=[CH:71][CH:72]=[CH:73][CH:74]=2)[N:69]([C:76](=[O:83])[C:77]2[CH:82]=[CH:81][CH:80]=[CH:79][CH:78]=2)[CH:68]=1)(=O)C1C=CC=CC=1>>[C:76]([N:69]1[C:70]2[C:75](=[CH:74][CH:73]=[CH:72][CH:71]=2)[C:67]([CH2:66][C:43]2([OH:42])[C:51]3[C:46](=[CH:47][CH:48]=[C:49]([CH3:52])[CH:50]=3)[N:45]([CH2:53][CH2:54][CH3:55])[C:44]2=[O:56])=[CH:68]1)(=[O:83])[C:77]1[CH:78]=[CH:79][CH:80]=[CH:81][CH:82]=1

Participants

4

Reactant 3

HCID 863014383-((1H-indol-3-yl)methyl)-5-chloro-2-oxo-1-propylindolin-3-yl benzoateHCID 90411032HCID 90411032, compoundHCID 904174755-Methyl-2-oxo-1-propylindolin-3-yl benzoate

Product 1

HCID 863012773-((1-benzoyl-1H-indol-3-yl)methyl)-3-hydroxy-5-methyl-1-propylindolin-2-one

Procedure

This compound was made in a method analogous to 3-((1H-indol-3-yl)methyl)-5-chloro-2-oxo-1-propylindolin-3-yl benzoate using 5-methyl-2-oxo-1-propylindolin-3-yl benzoate and (1-benzoyl-1H-indol-3-yl)methyl benzoate. 1H-NMR δ 8.33 (d, 1H), 7.53 (m, 2H), 7.45-7.39 (m, 4H), 7.31 (dd, 1H), 7.29 (m, 1H), 7.17 (s, 1H), 7.08 (d, 1H), 6.59 (m, 2H), 3.53 (m, 1H), 3.40 (d, 1H), 3.29 (d, 1H), 3.20 (m, 1H), 2.77 (s, OH), 2.30 (s, 3H), 1.15 (m, 2H), 0.56 (t, 3H). Calculated mass for C28H26N2O3, 438.19. Observed 461.2 (M+Na).

Sources & evidence

ORD record
ord-11e11d3323404a628aa6c6e21ffb2c25
Source dataset
uspto-grants-2015_07
Patent number
US09079853B2

Reaction notes

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