3,4-Difluorobenzeneboronic acid → 6-(2-morpholinoethoxy)-3-(4-chlorophenyl)-2-(3,4-difluorophenyl)-1H-inden-1-one

HRID 331276Notes

Reaction equation

HRID 331276 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]1[CH:56]=[C:57](B(O)O)[CH:58]=[CH:59][C:60]=1[F:61]>>[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:58]4[CH:57]=[CH:56][C:55]([F:54])=[C:60]([F:61])[CH:59]=4)[C:16]3=[O:19])=[CH:12][CH:11]=2)[CH2:3][CH2:2]1

Participants

4

Reactant 3

HCID 27343373,4-Difluorobenzeneboronic 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 510024076-(2-morpholinoethoxy)-3-(4-chlorophenyl)-2-(3,4-difluorophenyl)-1H-inden-1-oneYield 43%

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, 3,4-difluorophenylboronic acid instead of 3-pyridinylboronic acid, and being purified by silica gel column chromatography (acetone/hexanes=1:4) to obtain the title compound (43%).

Workup

  1. custombeing purified by silica gel column chromatography (acetone/hexanes=1:4)

Sources & evidence

ORD record
ord-766ab4238a6c4bf2b701cbde5941b251
Source dataset
uspto-grants-2014_11
Patent number
US08877747B2

Reaction notes

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