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

HRID 331339Notes

Reaction equation

HRID 331339 reaction equation
Br[C:2]1[C:3](=[O:30])[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][S:25](=[O:29])(=[O:28])[CH2:24][CH2:23]1)[CH:5]=2.O1CCN(CCO[C:40]2[CH:48]=[C:47]3[C:43]([C:44](C4C=CC=CC=4)=C(Br)C3=O)=[CH:42][CH:41]=2)CC1.B(O)(O)C1C=CC(C)=CC=1>>[F:17][C:15]1[CH:16]=[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][S:25](=[O:29])(=[O:28])[CH2:26][CH2:27]4)=[CH:7][CH:8]=3)[C:3](=[O:30])[C:2]=2[C:40]2[CH:48]=[CH:47][C:43]([CH3:44])=[CH:42][CH:41]=2)[CH:12]=[C:13]([F:18])[CH:14]=1

Participants

4

Reactant 3

HCID 79799Tolylboronic acidHCID 703076206-(2-morpholinoethoxy)-2-bromo-3-phenyl-1H-inden-1-oneHCID 703123362-Bromo-3-(3,5-difluorophenyl)-6-[2-(1,1-dioxothiomorpholin-4-yl)ethoxy]-1H-inden-1-one

Product 1

HCID 681813813-(3,5-Difluorophenyl)-6-[2-(1,1-dioxothiomorpholin-4-yl)ethoxy]-2-p-tolyl-1H-inden-1-oneYield 71%

Procedure

The procedure of Step 7 of Example 1 was repeated except for using 2-bromo-3-(3,5-difluorophenyl)-6-[2-(1,1-dioxothiomorpholin-4-yl)ethoxy]-1H-inden-1-one obtained in Step 1 of Example 92 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/hexanes=1:1) to obtain the title compound (71%).

Workup

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

Sources & evidence

ORD record
ord-36020f48383c46379a1f842147b8dde2
Source dataset
uspto-grants-2014_11
Patent number
US08877747B2

Reaction notes

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