3-Fluoro-4-methoxyphenylboronic acid → 2-(3-fluoro-4-methoxyphenyl)-3-(2,4-difluorophenyl)-6-{3-[4-(methylsulfonyl)piperazin-1-yl]propoxy}-1H-inden-1-one

HRID 331368Notes

Reaction equation

HRID 331368 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.[F:60][C:61]1[CH:62]=[C:63](B(O)O)[CH:64]=[CH:65][C:66]=1[O:67][CH3:68]>>[F:60][C:61]1[CH:62]=[C:63]([C:2]2[C:3](=[O:33])[C:4]3[C:9]([C:10]=2[C:11]2[CH:16]=[CH:15][C:14]([F:17])=[CH:13][C:12]=2[F:18])=[CH:8][CH:7]=[C:6]([O:19][CH2:20][CH2:21][CH2:22][N:23]2[CH2:24][CH2:25][N:26]([S:29]([CH3:32])(=[O:31])=[O:30])[CH2:27][CH2:28]2)[CH:5]=3)[CH:64]=[CH:65][C:66]=1[O:67][CH3:68]

Participants

4

Reactant 3

HCID 27821943-Fluoro-4-methoxyphenylboronic acidHCID 703076206-(2-morpholinoethoxy)-2-bromo-3-phenyl-1H-inden-1-oneHCID 70312831HCID 70312831, compound

Product 1

HCID 703143192-(3-fluoro-4-methoxyphenyl)-3-(2,4-difluorophenyl)-6-{3-[4-(methylsulfonyl)piperazin-1-yl]propoxy}-1H-inden-1-oneYield 77%

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-fluoro-4-methoxyphenylboronic acid instead of 3-pyridinylboronic acid to obtain the title compound (77%).

Sources & evidence

ORD record
ord-9f0158f976724196ae1d60e38ec77efb
Source dataset
uspto-grants-2014_11
Patent number
US08877747B2

Reaction notes

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