Quinoline-3-boronic acid → 3-(2,4-difluorophenyl)-6-{3-[4-(methylsulfonyl)piperazin-1-yl]propoxy}-2-(quinolin-3-yl)-1H-inden-1-one

HRID 331369Notes

Reaction equation

HRID 331369 reaction equation
Br[C:2]1[C:3](=[O:33])[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][CH2:22][N:23]1[CH2:28][CH2:27][N:26]([S:29]([CH3:32])(=[O:31])=[O:30])[CH2:25][CH2:24]1)[CH:5]=2.O1CCN(CCOC2C=C3C(C(C4C=CC=CC=4)=C(Br)C3=O)=CC=2)CC1.[N:60]1[C:69]2[C:64](=[CH:65][CH:66]=[CH:67][CH:68]=2)[CH:63]=[C:62](B(O)O)[CH:61]=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][CH2:22][N:23]3[CH2:28][CH2:27][N:26]([S:29]([CH3:32])(=[O:31])=[O:30])[CH2:25][CH2:24]3)=[CH:7][CH:8]=2)[C:3](=[O:33])[C:2]=1[C:62]1[CH:61]=[N:60][C:69]2[C:64]([CH:63]=1)=[CH:65][CH:66]=[CH:67][CH:68]=2

Participants

4

Reactant 3

HCID 2734663Quinoline-3-boronic acidHCID 703076206-(2-morpholinoethoxy)-2-bromo-3-phenyl-1H-inden-1-oneHCID 70312831HCID 70312831, compound

Product 1

HCID 510022413-(2,4-difluorophenyl)-6-{3-[4-(methylsulfonyl)piperazin-1-yl]propoxy}-2-(quinolin-3-yl)-1H-inden-1-oneYield 83%

Procedure

The procedure of Step 7 of Example 1 was repeated except for using 2-bromo-3-(2,4-difluorophenyl)-6-[3-(4-(methylsulfonyl)piperazin-1-yl)propoxy]-1H-inden-1-one obtained in Step 1 of Example 108 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 (83%).

Sources & evidence

ORD record
ord-0465f1e07eeb439092cb331d830538df
Source dataset
uspto-grants-2014_11
Patent number
US08877747B2

Reaction notes

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