2-(Dimethylamino)ethanol → 6-(2-(Dimethylamino)ethoxy)-3-phenyl-2-(pyridin-3-yl)-1H-inden-1-one

HRID 331306Notes

Reaction equation

HRID 331306 reaction equation
[OH:1][C:2]1[CH:10]=[C:9]2[C:5]([C:6]([C:18]3[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=3)=[C:7]([C:12]3[CH:13]=[N:14][CH:15]=[CH:16][CH:17]=3)[C:8]2=[O:11])=[CH:4][CH:3]=1.BrC1C(=O)C2C(C=1C1C=CC=CC=1)=CC=C(O)C=2.[CH3:42][N:43]([CH3:47])[CH2:44][CH2:45]O>>[CH3:42][N:43]([CH3:47])[CH2:44][CH2:45][O:1][C:2]1[CH:10]=[C:9]2[C:5]([C:6]([C:18]3[CH:19]=[CH:20][CH:21]=[CH:22][CH:23]=3)=[C:7]([C:12]3[CH:13]=[N:14][CH:15]=[CH:16][CH:17]=3)[C:8]2=[O:11])=[CH:4][CH:3]=1

Participants

4

Reactant 3

HCID 79022-(Dimethylamino)ethanolHCID 703061762-bromo-6-hydroxy-3-phenyl-1H-inden-1-oneHCID 703131906-Hydroxy-3-phenyl-2-(pyridin-3-yl)-1H-inden-1-one

Product 1

HCID 510018356-(2-(Dimethylamino)ethoxy)-3-phenyl-2-(pyridin-3-yl)-1H-inden-1-oneYield 45%

Procedure

The procedure of Step 6 of Example 1 was repeated except for using 6-hydroxy-3-phenyl-2-(pyridin-3-yl)-1H-inden-1-one obtained in Step 1 of Example 55 as a starting material instead of 2-bromo-6-hydroxy-3-phenyl-1H-inden-1-one, 2-(dimethylamino)ethanol instead of 4-(2-hydroxyethyl)morpholine, and being recrystallized with EtOAc to obtain the title compound (45%).

Workup

  1. custombeing recrystallized with EtOAc

Sources & evidence

ORD record
ord-299228a248794e1a9ec82e0398d18846
Source dataset
uspto-grants-2014_11
Patent number
US08877747B2

Reaction notes

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