3-(Dimethylamino)-1-propanol → 6-(3-(Dimethylamino)propoxy)-3-phenyl-2-(pyridin-3-yl)-1H-inden-1-one

HRID 331307Notes

Reaction equation

HRID 331307 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]([CH3:48])[CH2:44][CH2:45][CH2:46]O>>[CH3:42][N:43]([CH3:48])[CH2:44][CH2:45][CH2:46][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 766463-(Dimethylamino)-1-propanolHCID 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 510018876-(3-(Dimethylamino)propoxy)-3-phenyl-2-(pyridin-3-yl)-1H-inden-1-oneYield 30%

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, 3-(dimethylamino)propanol instead of 4-(2-hydroxyethyl)morpholine, being stirred for 4 d, and being recrystallized with EtOAc to obtain the title compound (30%).

Workup

  1. custombeing recrystallized with EtOAc

Sources & evidence

ORD record
ord-ed5c4661e4ee4e56b5d718c5ec51843c
Source dataset
uspto-grants-2014_11
Patent number
US08877747B2

Reaction notes

Loading…