3,4-Difluorobenzeneboronic acid → HCID 51002537, compound

HRID 331296Notes

Reaction equation

HRID 331296 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]1[CH:63]=[C:64](B(O)O)[CH:65]=[CH:66][C:67]=1[F:68]>>[F:61][C:62]1[CH:63]=[C:64]([C:2]2[C:3](=[O:34])[C:4]3[C:9]([C:10]=2[C:11]2[CH:16]=[CH:15][C:14]([C:17]([F:20])([F:18])[F:19])=[CH:13][CH:12]=2)=[CH:8][CH:7]=[C:6]([O:21][CH2:22][CH2:23][N:24]2[CH2:29][CH2:28][N:27]([S:30]([CH3:33])(=[O:32])=[O:31])[CH2:26][CH2:25]2)[CH:5]=3)[CH:65]=[CH:66][C:67]=1[F:68]

Participants

4

Reactant 3

HCID 27343373,4-Difluorobenzeneboronic acidHCID 703076206-(2-morpholinoethoxy)-2-bromo-3-phenyl-1H-inden-1-oneHCID 70308159HCID 70308159, compound

Product 1

HCID 51002537HCID 51002537, compoundYield 49%

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 of Example 47 as a starting material instead of 6-(2-morpholinoethoxy)-2-bromo-3-phenyl-1H-inden-1-one, and 3,4-difluorophenylboronic acid instead of 3-pyridinylboronic acid, and being purified by prep HPLC (CH3CN/H2O=7:3) to obtain the title compound (49%).

Workup

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

Sources & evidence

ORD record
ord-010647bdd9bc407081d3e19613ee115d
Source dataset
uspto-grants-2014_11
Patent number
US08877747B2

Reaction notes

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