4-(Trifluoromethyl)phenylboronic acid → HCID 51002535, compound

HRID 331295Notes

Reaction equation

HRID 331295 reaction equation
Br[C:2]1[C:3](=[O:34])[C:4]2[C:9]([C:10]=1[C:11]1[CH:16]=[CH:15][C:14]([C:17]([F:20])([F:19])[F:18])=[CH:13][CH:12]=1)=[CH:8][CH:7]=[C:6]([O:21][CH2:22][CH2:23][N:24]1[CH2:29][CH2:28][N:27]([S:30]([CH3:33])(=[O:32])=[O:31])[CH2:26][CH2:25]1)[CH:5]=2.O1CCN(CCOC2C=C3C(C(C4C=CC=CC=4)=C(Br)C3=O)=CC=2)CC1.[F:61][C:62]([F:73])([F:72])[C:63]1[CH:68]=[CH:67][C:66](B(O)O)=[CH:65][CH:64]=1>>[CH3:33][S:30]([N:27]1[CH2:26][CH2:25][N:24]([CH2:23][CH2:22][O:21][C:6]2[CH:5]=[C:4]3[C:9]([C:10]([C:11]4[CH:12]=[CH:13][C:14]([C:17]([F:19])([F:20])[F:18])=[CH:15][CH:16]=4)=[C:2]([C:66]4[CH:67]=[CH:68][C:63]([C:62]([F:73])([F:72])[F:61])=[CH:64][CH:65]=4)[C:3]3=[O:34])=[CH:8][CH:7]=2)[CH2:29][CH2:28]1)(=[O:31])=[O:32]

Participants

4

Reactant 3

HCID 27343894-(Trifluoromethyl)phenylboronic acidHCID 703076206-(2-morpholinoethoxy)-2-bromo-3-phenyl-1H-inden-1-oneHCID 70308159HCID 70308159, compound

Product 1

HCID 51002535HCID 51002535, compoundYield 21%

Procedure

The procedure of Step 7 of Example 1 was repeated except for using 2-bromo-6-[2-(4-(methylsulfonyl)piperazin-1-yl)ethoxy]-3-[4-(trifluoromethyl)phenyl]-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, and 4-(trifluoromethyl)phenylboronic acid instead of 3-pyridinylboronic acid, and being purified by prep HPLC (CH3CN/H2O=7:3) to obtain the title compound (21%).

Workup

  1. custombeing purified by prep HPLC (CH3CN/H2O=7:3)

Sources & evidence

ORD record
ord-46e8b7f9f8004776ba87843aec232e91
Source dataset
uspto-grants-2014_11
Patent number
US08877747B2

Reaction notes

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