Potassium Phosphate, Tribasic → 4-cyclopropyl-N-(3-(dimethylamino)propyl)-N-methyl-2-nitrobenzenamine
Reaction equation
C1(B2O[C:7]([CH3:10])([CH3:9])[C:6]([CH3:12])([CH3:11])O2)CC1.P([O-])([O-])([O-])=O.[K+].[K+].[K+].BrC1C=[CH:26][C:25]([N:28]([CH3:35])[CH2:29][CH2:30][CH2:31][N:32]([CH3:34])[CH3:33])=[C:24]([N+:36]([O-:38])=[O:37])C=1.C1(P(C2CCCCC2)C2CCCCC2)CCCCC1>C([O-])(=O)C.[Pd+2].C([O-])(=O)C.C1(C)C=CC=CC=1.O>[CH:6]1([C:7]2[CH:9]=[CH:26][C:25]([N:28]([CH2:29][CH2:30][CH2:31][N:32]([CH3:34])[CH3:33])[CH3:35])=[C:24]([N+:36]([O-:38])=[O:37])[CH:10]=2)[CH2:11][CH2:12]1Participants
Reactant 4
Product 1
Reagents, catalysts & solvents 3
Procedure
To a pressure vessel was added 2-cyclopropyl-4,4,5,5-tetramethyl-1,3,2-dioxaborolane (900 mg, 5.36 mmol), potassium phosphate (3.0 g, 14.42 mmol), and 0.82 mL water. After stirring at RT for 15 minutes, N-(4-Bromo-2-nitro-phenyl)-N,N′,N′-trimethyl-propane-1,3-diamine (Step 1, 1.30 g, 4.12 mmol), palladium acetate (92 mg, 0.412 mmol), tricyclohexylphosphine (231 mg 0.824 mmol), and 21 ml toluene were added. The reaction was sealed and stirred at 80° C. for 19 h. The reaction was then cooled to RT, quenched with EtOAc and extracted into water, washed once with brine, and then dried over Mg2SO4. The crude mixture was then purified by reverse phase chromatography to yield the title compound as a dark red-brown oil. MS (M+H−)=278; Calc'd for C15H23N3O2=277.36.
Workup
- customThe reaction was sealed
- stirringstirred at 80° C. for 19 h
- temperatureThe reaction was then cooled to RT
- customquenched with EtOAc
- extractionextracted into water
- washwashed once with brine
- dry with materialdried over Mg2SO4
- customThe crude mixture was then purified by reverse phase chromatography
Sources & evidence
- ORD record
- ord-55b5b722ee9e46148069d7b9797f82f0
- Source dataset
- uspto-grants-2013_10
- Patent number
- US08557996B2
Reaction notes
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