Ethyl Acetate → HCID 22329191, compound

HRID 586828Notes

Reaction equation

HRID 586828 reaction equation
Br[C:2]1[CH:3]=[CH:4][C:5]2[N:11]([CH3:12])[CH2:10][CH2:9][C:8]([C:13]([NH:15][C:16]3[CH:21]=[CH:20][C:19]([CH2:22][N:23]([CH3:30])[CH:24]4[CH2:29][CH2:28][O:27][CH2:26][CH2:25]4)=[CH:18][CH:17]=3)=[O:14])=[CH:7][C:6]=2[CH:31]=1.C(=O)([O-])[O-].[K+].[K+].C(O[CH2:42][CH3:43])(=O)C>O.C(O)C.C1(C)C=CC=CC=1.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[CH2:10]([N:11]([CH2:42][CH3:43])[C:5]1[CH:6]=[CH:31][C:2]([C:2]2[CH:3]=[CH:4][C:5]3[N:11]([CH3:12])[CH2:10][CH2:9][C:8]([C:13]([NH:15][C:16]4[CH:21]=[CH:20][C:19]([CH2:22][N:23]([CH3:30])[CH:24]5[CH2:25][CH2:26][O:27][CH2:28][CH2:29]5)=[CH:18][CH:17]=4)=[O:14])=[CH:7][C:6]=3[CH:31]=2)=[CH:3][CH:4]=1)[CH3:9]

Participants

6

Reactant 3

HCID 8857Ethyl AcetateHCID 11430Potassium CarbonateHCID 223290367-bromo-1-methyl-N-[4-[[N-methyl-N-(tetrahydropyran-4-yl)amino]methyl]phenyl]-2,3-dihydro-1-benzoazepine-4-carboxamide

Product 1

HCID 22329191HCID 22329191, compoundYield 33%

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 86587398Ethanol toluene waterSolvent

Procedure

In water:ethanol:toluene (1:1:10, v/v, 18.0 ml) were dissolved (4-diethylamino)phenyl borate (234 mg) and 7-bromo-1-methyl-N-[4-[[N-methyl-N-(tetrahydro-2H-pyran-4-yl)amino]methyl]phenyl]-2,3-dihydro-1H-1-benzazepine-4-carboxamide (391 mg). To the solution was added potassium carbonate (268 mg), and the mixture was stirred under argon atmosphere at room temperature for 30 minutes. To the mixture was added tetrakistriphenylphosphinepalladium (37 mg), and the mixture was heated to reflux under argon atmosphere for 10 hours. The mixture was diluted with ethyl acetate, and washed with water and saturated brine, and the organic layer was dried with anhydrous magnesium sulfate. The solvent was evaporated under reduced pressure, and the residue was purified with silica gel column chromatography (45 g, ethyl acetate:ethanol=20:1) and recrystallized from ethanol to give 7-(4-diethylaminophenyl)-1-methyl-N-(4-[[N-methyl-N-(tetrahydro-2H-pyran-4-yl)amino]methyl]phenyl]-2,3-dihydro-1H-1-benzazepine-4-carboxamide (145 mg, 33%) as yellow crystals.

Workup

  1. temperaturethe mixture was heated
  2. temperatureto reflux under argon atmosphere for 10 hours
  3. washwashed with water and saturated brine
  4. dry with materialthe organic layer was dried with anhydrous magnesium sulfate
  5. customThe solvent was evaporated under reduced pressure
  6. customthe residue was purified with silica gel column chromatography (45 g, ethyl acetate:ethanol=20:1)
  7. customrecrystallized from ethanol

Sources & evidence

ORD record
ord-b3d8c6ad13a347b390f599410db51c23
Source dataset
uspto-grants-2005_08
Patent number
US06936602B1

Reaction notes

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