Quinoline-3-boronic acid → HCID 51002237, compound

HRID 331337Notes

Reaction equation

HRID 331337 reaction equation
Br[C:2]1[C:3](=[O:30])[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][S:25](=[O:29])(=[O:28])[CH2:24][CH2:23]1)[CH:5]=2.O1CCN(CCOC2C=C3C(C(C4C=CC=CC=4)=C(Br)C3=O)=CC=2)CC1.[N:57]1[C:66]2[C:61](=[CH:62][CH:63]=[CH:64][CH:65]=2)[CH:60]=[C:59](B(O)O)[CH:58]=1>>[F:18][C:13]1[CH:12]=[C:11]([C:10]2[C:9]3[C:4](=[CH:5][C:6]([O:19][CH2:20][CH2:21][N:22]4[CH2:27][CH2:26][S:25](=[O:29])(=[O:28])[CH2:24][CH2:23]4)=[CH:7][CH:8]=3)[C:3](=[O:30])[C:2]=2[C:59]2[CH:58]=[N:57][C:66]3[C:61]([CH:60]=2)=[CH:62][CH:63]=[CH:64][CH:65]=3)[CH:16]=[C:15]([F:17])[CH:14]=1

Participants

4

Reactant 3

HCID 2734663Quinoline-3-boronic acidHCID 703076206-(2-morpholinoethoxy)-2-bromo-3-phenyl-1H-inden-1-oneHCID 703123362-Bromo-3-(3,5-difluorophenyl)-6-[2-(1,1-dioxothiomorpholin-4-yl)ethoxy]-1H-inden-1-one

Product 1

HCID 51002237HCID 51002237, compoundYield 95%

Procedure

The procedure of Step 7 of Example 1 was repeated except for using 2-bromo-3-(3,5-difluorophenyl)-6-[2-(1,1-dioxothiomorpholin-4-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-quinolinylboronic acid instead of 3-pyridinylboronic acid and being purified by silica gel column chromatography (acetone/hexanes=1:3) to obtain the title compound (95%).

Workup

  1. custombeing purified by silica gel column chromatography (acetone/hexanes=1:3)

Sources & evidence

ORD record
ord-fed52fb0a77c476a817ef534e636fd6d
Source dataset
uspto-grants-2014_11
Patent number
US08877747B2

Reaction notes

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