4-(Trifluoromethyl)phenylboronic acid → 6-(2-morpholinoethoxy)-3-(4-chlorophenyl)-2-(4-(trifluoromethyl)phenyl)-1H-inden-1-one

HRID 331278Notes

Reaction equation

HRID 331278 reaction equation
[O:1]1[CH2:6][CH2:5][N:4]([CH2:7][CH2:8][O:9][C:10]2[CH:18]=[C:17]3[C:13]([C:14]([C:21]4[CH:26]=[CH:25][C:24]([Cl:27])=[CH:23][CH:22]=4)=[C:15](Br)[C:16]3=[O:19])=[CH:12][CH:11]=2)[CH2:3][CH2:2]1.O1CCN(CCOC2C=C3C(C(C4C=CC=CC=4)=C(Br)C3=O)=CC=2)CC1.[F:54][C:55]([F:66])([F:65])[C:56]1[CH:61]=[CH:60][C:59](B(O)O)=[CH:58][CH:57]=1>>[O:1]1[CH2:6][CH2:5][N:4]([CH2:7][CH2:8][O:9][C:10]2[CH:18]=[C:17]3[C:13]([C:14]([C:21]4[CH:26]=[CH:25][C:24]([Cl:27])=[CH:23][CH:22]=4)=[C:15]([C:59]4[CH:60]=[CH:61][C:56]([C:55]([F:66])([F:65])[F:54])=[CH:57][CH:58]=4)[C:16]3=[O:19])=[CH:12][CH:11]=2)[CH2:3][CH2:2]1

Participants

4

Reactant 3

HCID 27343894-(Trifluoromethyl)phenylboronic acidHCID 703076206-(2-morpholinoethoxy)-2-bromo-3-phenyl-1H-inden-1-oneHCID 703123176-(2-Morpholino ethoxy)-2-bromo-3-(4-chlorophenyl)-1H-inden-1-one

Product 1

HCID 510024896-(2-morpholinoethoxy)-3-(4-chlorophenyl)-2-(4-(trifluoromethyl)phenyl)-1H-inden-1-oneYield 14%

Procedure

The procedure of Step 7 of Example 1 was repeated except for using 6-(2-morpholinoethoxy)-2-bromo-3-(4-chlorophenyl)-1H-inden-1-one obtained in Step 6 of Example 28 as a starting material instead of 6-(2-morpholinoethoxy)-2-bromo-3-phenyl-1H-inden-1-one, 4-(trifluoromethyl)phenyboronic acid instead of 3-pyridinylboronic acid, and being purified by prep HPLC (CH3CN/H2O=7:3) to obtain the title compound (14%).

Workup

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

Sources & evidence

ORD record
ord-76a425db33ad46bf9d7a5ae0759ae815
Source dataset
uspto-grants-2014_11
Patent number
US08877747B2

Reaction notes

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