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Potassium Phosphate, Tribasic → 4-cyclopropyl-N-(3-(dimethylamino)propyl)-N-methyl-2-nitrobenzenamine

HRID 1042695
Notes
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Reaction equation

HRID 1042695 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]1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

8

Reactant 4

HCID 62657Potassium Phosphate, TribasicHCID 75806TricyclohexylphosphineHCID 27580152-Cyclopropyl-4,4,5,5-tetramethyl-1,3,2-dioxaborolaneHCID 16109013HCID 16109013, compound

Product 1

HCID 161090144-cyclopropyl-N-(3-(dimethylamino)propyl)-N-methyl-2-nitrobenzenamine

Reagents, catalysts & solvents 3

HCID 167845palladium(II) acetateCatalyst
HCID 962WaterSolvent
HCID 1140TolueneSolvent

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

  1. customThe reaction was sealed
  2. stirringstirred at 80° C. for 19 h
  3. temperatureThe reaction was then cooled to RT
  4. customquenched with EtOAc
  5. extractionextracted into water
  6. washwashed once with brine
  7. dry with materialdried over Mg2SO4
  8. customThe crude mixture was then purified by reverse phase chromatography

Sources & evidence

ORD record
ord-55b5b722ee9e46148069d7b9797f82f0
Source dataset
uspto-grants-2013_10
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08557996B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes