3,4-Difluorobenzeneboronic acid → HCID 51002491, compound

HRID 331289Notes

Reaction equation

HRID 331289 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]=[C:25]([F:27])[CH:24]=[C:23]([F:28])[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:55][C:56]1[CH:57]=[C:58](B(O)O)[CH:59]=[CH:60][C:61]=1[F:62]>>[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]=[C:25]([F:27])[CH:24]=[C:23]([F:28])[CH:22]=4)=[C:15]([C:59]4[CH:58]=[CH:57][C:56]([F:55])=[C:61]([F:62])[CH:60]=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 70313397HCID 70313397, compound

Product 1

HCID 51002491HCID 51002491, compoundYield 47%

Procedure

The procedure of Step 7 of Example 1 was repeated except for using 6-(2-morpholinoethoxy)-2-bromo-3-(3,5-difluorophenyl)-1H-inden-1-one obtained in Step 6 of Example 36 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 (47%).

Workup

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

Sources & evidence

ORD record
ord-24425225b4f8448381414ea7c579ad83
Source dataset
uspto-grants-2014_11
Patent number
US08877747B2

Reaction notes

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