2-(4-(Methylsulfonyl)piperazin-1-yl)ethanol → 2-Bromo-3-(3,5-difluorophenyl)-6-(2-(4-(methylsulfonyl)piperazin-1-yl)ethoxy)-1H-inden-1-one

HRID 331341Notes

Reaction equation

HRID 331341 reaction equation
[Br:1][C:2]1[C:3](=[O:20])[C:4]2[C:9]([C:10]=1[C:11]1[CH:16]=[C:15]([F:17])[CH:14]=[C:13]([F:18])[CH:12]=1)=[CH:8][CH:7]=[C:6]([OH:19])[CH:5]=2.BrC1C(=O)C2C(C=1C1C=CC=CC=1)=CC=C(O)C=2.[CH3:39][S:40]([N:43]1[CH2:48][CH2:47][N:46]([CH2:49][CH2:50]O)[CH2:45][CH2:44]1)(=[O:42])=[O:41]>>[Br:1][C:2]1[C:3](=[O:20])[C:4]2[C:9]([C:10]=1[C:11]1[CH:12]=[C:13]([F:18])[CH:14]=[C:15]([F:17])[CH:16]=1)=[CH:8][CH:7]=[C:6]([O:19][CH2:50][CH2:49][N:46]1[CH2:47][CH2:48][N:43]([S:40]([CH3:39])(=[O:41])=[O:42])[CH2:44][CH2:45]1)[CH:5]=2

Participants

4

Reactant 3

HCID 27624262-(4-(Methylsulfonyl)piperazin-1-yl)ethanolHCID 703061762-bromo-6-hydroxy-3-phenyl-1H-inden-1-oneHCID 703160432-Bromo-3-(3,5-difluorophenyl)-6-hydroxy-1H-inden-1-one

Product 1

HCID 703100942-Bromo-3-(3,5-difluorophenyl)-6-(2-(4-(methylsulfonyl)piperazin-1-yl)ethoxy)-1H-inden-1-oneYield 73%

Procedure

The procedure of Step 6 of Example 1 was repeated except for using 2-bromo-3-(3,5-difluorophenyl)-6-hydroxy-1H-inden-1-one obtained in Step 5 of Example 36 as a starting material instead of 2-bromo-6-hydroxy-3-phenyl-1H-inden-1-one, 2-(4-(methylsulfonyl)piperazin-1-yl)ethanol instead of 4-(2-hydroxyethyl)morpholine, being stirred for 2 h, and being purified by silica gel column chromatography (acetone/hexanes=2:1) to obtain the title compound (73%).

Workup

  1. custombeing purified by silica gel column chromatography (acetone/hexanes=2:1)

Sources & evidence

ORD record
ord-1f101f787d164b22963f0f6d3371509a
Source dataset
uspto-grants-2014_11
Patent number
US08877747B2

Reaction notes

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