3-Fluoro-4-methylbenzeneboronic acid → 2-(3-Fluoro-4-methylphenyl)-5-Methoxy-3-phenyl-1H-inden-1-one

HRID 331395Notes

Reaction equation

HRID 331395 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(CCOC2C=C3C(C(C4C=CC=CC=4)=C(Br)C3=O)=CC=2)CC1.[F:46][C:47]1[CH:48]=[C:49](B(O)O)[CH:50]=[CH:51][C:52]=1[CH3:53]>>[F:46][C:47]1[CH:48]=[C:49]([C:2]2[C:3](=[O:19])[C:4]3[C:9]([C:10]=2[C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)=[CH:8][C:7]([O:17][CH3:18])=[CH:6][CH:5]=3)[CH:50]=[CH:51][C:52]=1[CH3:53]

Participants

4

Reactant 3

HCID 27826743-Fluoro-4-methylbenzeneboronic acidHCID 104709362-Bromo-5-methoxy-3-phenyl-1H-inden-1-oneHCID 703076206-(2-morpholinoethoxy)-2-bromo-3-phenyl-1H-inden-1-one

Product 1

HCID 703171212-(3-Fluoro-4-methylphenyl)-5-Methoxy-3-phenyl-1H-inden-1-oneYield 65%

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, 3-fluoro-4-methylphenylboronic acid instead of 3-pyridinylboronic acid, and being stirred for 10 min to obtain the title compound (65%).

Sources & evidence

ORD record
ord-351b26f83a9c4733b8cd5a25821551eb
Source dataset
uspto-grants-2014_11
Patent number
US08877747B2

Reaction notes

Loading…