3,4-Difluorobenzeneboronic acid → 3-(4-Chlorophenyl)-2-(3,4-difluorophenyl)-6-(2-(4-(methylsulfonyl)piperazin-1-yl)ethoxy)-1H-inden-1-one

HRID 331301Notes

Reaction equation

HRID 331301 reaction equation
Br[C:2]1[C:3](=[O:31])[C:4]2[C:9]([C:10]=1[C:11]1[CH:16]=[CH:15][C:14]([Cl:17])=[CH:13][CH:12]=1)=[CH:8][CH:7]=[C:6]([O:18][CH2:19][CH2:20][N:21]1[CH2:26][CH2:25][N:24]([S:27]([CH3:30])(=[O:29])=[O:28])[CH2:23][CH2:22]1)[CH:5]=2.O1CCN(CCOC2C=C3C(C(C4C=CC=CC=4)=C(Br)C3=O)=CC=2)CC1.[F:58][C:59]1[CH:60]=[C:61](B(O)O)[CH:62]=[CH:63][C:64]=1[F:65]>>[Cl:17][C:14]1[CH:13]=[CH:12][C:11]([C:10]2[C:9]3[C:4](=[CH:5][C:6]([O:18][CH2:19][CH2:20][N:21]4[CH2:22][CH2:23][N:24]([S:27]([CH3:30])(=[O:29])=[O:28])[CH2:25][CH2:26]4)=[CH:7][CH:8]=3)[C:3](=[O:31])[C:2]=2[C:62]2[CH:61]=[CH:60][C:59]([F:58])=[C:64]([F:65])[CH:63]=2)=[CH:16][CH:15]=1

Participants

4

Reactant 3

HCID 27343373,4-Difluorobenzeneboronic acidHCID 703076206-(2-morpholinoethoxy)-2-bromo-3-phenyl-1H-inden-1-oneHCID 703144382-Bromo-3-(4-chlorophenyl)-6-(2-(4-(methylsulfonyl)piperazin-1-yl)ethoxy)-1H-inden-1-one

Product 1

HCID 510018323-(4-Chlorophenyl)-2-(3,4-difluorophenyl)-6-(2-(4-(methylsulfonyl)piperazin-1-yl)ethoxy)-1H-inden-1-oneYield 50%

Procedure

The procedure of Step 7 of Example 1 was repeated except for using 2-bromo-3-(4-chlorophenyl)-6-(2-(4-(methylsulfonyl)piperazin-1-yl)ethoxy)-1H-inden-1-one obtained in Step 1 as a starting material instead of 6-(2-morpholinoethoxy)-2-bromo-3-phenyl-1H-inden-1-one, 3,4-difluorophenylboronic acid instead of 3-pyridinylboronic acid, and being purified by prep HPLC (CH3CN/H2O=7:3) to obtain the title compound (50%).

Workup

  1. custombeing purified by prep HPLC (CH3CN/H2O=7:3)

Sources & evidence

ORD record
ord-84e45116e7c94c70a931eea9584d447f
Source dataset
uspto-grants-2014_11
Patent number
US08877747B2

Reaction notes

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