Dimethyl Sulfoxide → 6-(3,5-dimethylisoxazol-4-yl)-4-(6-(trifluoromethoxy)quinolin-5-yl)-1H-benzo[d]imidazol-2(3H)-one
Reaction equation
Br[C:2]1[C:11]([O:12][C:13]([F:16])([F:15])[F:14])=[CH:10][CH:9]=[C:8]2[C:3]=1[CH:4]=[CH:5][CH:6]=[N:7]2.[CH3:17][C:18]1[C:22]([C:23]2[CH:24]=[C:25](B3OC(C)(C)C(C)(C)O3)[C:26]3[NH:30][C:29](=[O:31])[NH:28][C:27]=3[CH:32]=2)=[C:21]([CH3:42])[O:20][N:19]=1.N12CCCN=C1CCCCC2.CS(C)=O>O>[CH3:17][C:18]1[C:22]([C:23]2[CH:24]=[C:25]([C:2]3[C:11]([O:12][C:13]([F:16])([F:15])[F:14])=[CH:10][CH:9]=[C:8]4[C:3]=3[CH:4]=[CH:5][CH:6]=[N:7]4)[C:26]3[NH:30][C:29](=[O:31])[NH:28][C:27]=3[CH:32]=2)=[C:21]([CH3:42])[O:20][N:19]=1Participants
6
Reactant 4
Product 1
Reagents, catalysts & solvents 1
Procedure
A solution of 5-bromo-6-(trifluoromethoxy)quinoline (obtained by bromination of 6-trifluoromethoxyquinoline) (50 mg, 0.17 mmol), 6-(3,5-dimethylisoxazol-4-yl)-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-benzo[d]imidazol-2(3H)-one (91 mg, 0.26 mmol), dichloro 1,1-bis(diphenylphosphino)ferrocene palladium(II) dichloromethane (12.7 mg, 0.02 mmol), 1,8-diazabicyclo[5.4.0]undec-7-ene (0.2 mL, 1.37 mmol), DMSO (0.2 mL) and water (0.2 mL) under nitrogen was heated at 120° C. for 1 h. The reaction mixture was filtered and purified by reverse-phase HPLC to give 6-(3,5-dimethylisoxazol-4-yl)-4-(6-(trifluoromethoxy)quinolin-5-yl)-1H-benzo[d]imidazol-2(3H)-one.
Workup
- filtrationThe reaction mixture was filtered
- custompurified by reverse-phase HPLC
Sources & evidence
- ORD record
- ord-2957d57c3fcc4d0f8c608f3ce818ada0
- Source dataset
- uspto-grants-2016_02
- Patent number
- US09255089B2
Reaction notes
Loading…