Tolylboronic acid → 5-Methoxy-3-phenyl-2-(p-tolyl)-1H-inden-1-one

HRID 331393Notes

Reaction equation

Br[C:2]1[C:3](=[O:19])[C:4]2[C:9]([C:10]=1[C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1)=[CH:8][C:7]([O:17][CH3:18])=[CH:6][CH:5]=2.O1CCN(CCO[C:29]2[CH:37]=[C:36]3[C:32]([C:33](C4C=CC=CC=4)=C(Br)C3=O)=[CH:31][CH:30]=2)CC1.B(O)(O)C1C=CC(C)=CC=1>>[CH3:18][O:17][C:7]1[CH:8]=[C:9]2[C:4](=[CH:5][CH:6]=1)[C:3](=[O:19])[C:2]([C:29]1[CH:37]=[CH:36][C:32]([CH3:33])=[CH:31][CH:30]=1)=[C:10]2[C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1

Participants

Reactant 3

HCID 79799Tolylboronic acid

HCID 104709362-Bromo-5-methoxy-3-phenyl-1H-inden-1-one

HCID 703076206-(2-morpholinoethoxy)-2-bromo-3-phenyl-1H-inden-1-one

Product 1

HCID 703128725-Methoxy-3-phenyl-2-(p-tolyl)-1H-inden-1-oneYield 70%

Procedure

The procedure of Step 7 of Example 1 was repeated except for using 2-bromo-5-methoxy-3-phenyl-1H-inden-1-one obtained in Step 4 of Example 129 as a starting material instead of 6-(2-morpholinoethoxy)-2-bromo-3-phenyl-1H-inden-1-one, p-tolylboronic acid instead of 3-pyridinylboronic acid, and being stirred for 10 min to obtain the title compound (70%).

Sources & evidence

ORD record: ord-1d6f4e9e214f4dd58f2bdf4dfb93b846
Source dataset: uspto-grants-2014_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08877747B2

Reaction notes

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