Quinoline-3-boronic acid → HCID 67639464, compound

HRID 331374Notes

Reaction equation

HRID 331374 reaction equation
Br[C:2]1[C:3](=[O:30])[C:4]2[C:9]([C:10]=1[C:11]1[CH:16]=[CH:15][C:14]([F:17])=[CH:13][C:12]=1[F:18])=[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:12]1[CH:13]=[C:14]([F:17])[CH:15]=[CH:16][C:11]=1[C:10]1[C:9]2[C:4](=[CH:5][C:6]([O:19][CH2:20][CH2:21][N:22]3[CH2:27][CH2:26][S:25](=[O:28])(=[O:29])[CH2:24][CH2:23]3)=[CH:7][CH:8]=2)[C:3](=[O:30])[C:2]=1[C:59]1[CH:58]=[N:57][C:66]2[C:61]([CH:60]=1)=[CH:62][CH:63]=[CH:64][CH:65]=2

Participants

4

Reactant 3

HCID 2734663Quinoline-3-boronic acidHCID 703076206-(2-morpholinoethoxy)-2-bromo-3-phenyl-1H-inden-1-oneHCID 703140382-Bromo-3-(2,4-difluorophenyl)-6-[2-(1,1-dioxothiomorpholin-4-yl)ethoxy]-1H-inden-1-one

Product 1

HCID 67639464HCID 67639464, compoundYield 74%

Procedure

The procedure of Step 7 of Example 1 was repeated except for using 2-bromo-3-(2,4-difluorophenyl)-6-[2-(1,1-dioxothiomorpholin-4-yl)ethoxy]-1H-inden-1-one obtained in Step 1 of Example 112 as a starting material instead of 6-(2-morpholinoethoxy)-2-bromo-3-phenyl-1H-inden-1-one and 3-quinolinylboronic acid instead of 3-pyridinylboronic acid to obtain the title compound (74%).

Sources & evidence

ORD record
ord-f55e771194f2452ea42fa38de5a18674
Source dataset
uspto-grants-2014_11
Patent number
US08877747B2

Reaction notes

Loading…