Tolylboronic acid → 3-(3,5-Difluorophenyl)-6-{2-[4-(methylsulfonyl)piperazin-1-yl]ethoxy}-2-p-tolyl-1H-inden-1-one

HRID 331344Notes

Reaction equation

HRID 331344 reaction equation
Br[C:2]1[C:3](=[O:32])[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]([O:19][CH2:20][CH2:21][N:22]1[CH2:27][CH2:26][N:25]([S:28]([CH3:31])(=[O:30])=[O:29])[CH2:24][CH2:23]1)[CH:5]=2.O1CCN(CCO[C:42]2[CH:50]=[C:49]3[C:45]([C:46](C4C=CC=CC=4)=C(Br)C3=O)=[CH:44][CH:43]=2)CC1.B(O)(O)C1C=CC(C)=CC=1>>[F:18][C:13]1[CH:12]=[C:11]([C:10]2[C:9]3[C:4](=[CH:5][C:6]([O:19][CH2:20][CH2:21][N:22]4[CH2:23][CH2:24][N:25]([S:28]([CH3:31])(=[O:30])=[O:29])[CH2:26][CH2:27]4)=[CH:7][CH:8]=3)[C:3](=[O:32])[C:2]=2[C:42]2[CH:50]=[CH:49][C:45]([CH3:46])=[CH:44][CH:43]=2)[CH:16]=[C:15]([F:17])[CH:14]=1

Participants

4

Reactant 3

HCID 79799Tolylboronic acidHCID 703076206-(2-morpholinoethoxy)-2-bromo-3-phenyl-1H-inden-1-oneHCID 703100942-Bromo-3-(3,5-difluorophenyl)-6-(2-(4-(methylsulfonyl)piperazin-1-yl)ethoxy)-1H-inden-1-one

Product 1

HCID 681813843-(3,5-Difluorophenyl)-6-{2-[4-(methylsulfonyl)piperazin-1-yl]ethoxy}-2-p-tolyl-1H-inden-1-oneYield 52%

Procedure

The procedure of Step 7 of Example 1 was repeated except for using 2-bromo-3-(3,5-difluorophenyl)-6-{2-[4-(methylsulfonyl)piperazin-1-yl]ethoxy}-1H-inden-1-one obtained in Step 1 of Example 96 as a starting material instead of 6-(2-morpholinoethoxy)-2-bromo-3-phenyl-1H-inden-1-one, p-tolylboronic acid instead of 3-pyridinylboronic acid, and being purified by silica gel column chromatography (EtOAc/CH2Cl2=1:1) to obtain the title compound (52%).

Workup

  1. custombeing purified by silica gel column chromatography (EtOAc/CH2Cl2=1:1)

Sources & evidence

ORD record
ord-9be5bbca54a949c1b36339b9378a616a
Source dataset
uspto-grants-2014_11
Patent number
US08877747B2

Reaction notes

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