3-Fluoro-4-methoxyphenylboronic acid → HCID 70308331, compound

HRID 331345Notes

Reaction equation

HRID 331345 reaction equation
Br[C:2]1[C:3](=[O:32])[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][N:25]([S:28]([CH3:31])(=[O:30])=[O:29])[CH2:24][CH2:23]1)[CH:5]=2.O1CCN(CCOC2C=C3C(C(C4C=CC=CC=4)=C(Br)C3=O)=CC=2)CC1.[F:59][C:60]1[CH:61]=[C:62](B(O)O)[CH:63]=[CH:64][C:65]=1[O:66][CH3:67]>>[F:59][C:60]1[CH:61]=[C:62]([C:2]2[C:3](=[O:32])[C:4]3[C:9]([C:10]=2[C:11]2[CH:12]=[C:13]([F:18])[CH:14]=[C:15]([F:17])[CH:16]=2)=[CH:8][CH:7]=[C:6]([O:19][CH2:20][CH2:21][N:22]2[CH2:23][CH2:24][N:25]([S:28]([CH3:31])(=[O:29])=[O:30])[CH2:26][CH2:27]2)[CH:5]=3)[CH:63]=[CH:64][C:65]=1[O:66][CH3:67]

Participants

4

Reactant 3

HCID 27821943-Fluoro-4-methoxyphenylboronic acidHCID 703076206-(2-morpholinoethoxy)-2-bromo-3-phenyl-1H-inden-1-oneHCID 703100942-Bromo-3-(3,5-difluorophenyl)-6-(2-(4-(methylsulfonyl)piperazin-1-yl)ethoxy)-1H-inden-1-one

Product 1

HCID 70308331HCID 70308331, compoundYield 71%

Procedure

The procedure of Step 7 of Example 1 was repeated except for using 2-bromo-3-(3,5-difluorophenyl)-6-{2-[4-(methylsulfonyl)piperazin-1-yl]ethoxy}-1H-inden-1-one obtained in Step 1 of Example 96 as a starting material instead of 6-(2-morpholinoethoxy)-2-bromo-3-phenyl-1H-inden-1-one, 3-fluoro-4-methoxyphenylboronic acid instead of 3-pyridinylboronic acid, and being purified by silica gel column chromatography (EtOAc/CH2Cl2=1:1) to obtain the title compound (71%).

Workup

  1. custombeing purified by silica gel column chromatography (EtOAc/CH2Cl2=1:1)

Sources & evidence

ORD record
ord-11e9a2bbbaa54d5aac0f54682697c07a
Source dataset
uspto-grants-2014_11
Patent number
US08877747B2

Reaction notes

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