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Potassium Carbonate → HCID 22329202, compound

HRID 586875
Notes
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Reaction equation

HRID 586875 reaction equation
B([O-])([O-])O[C:3]1[CH:8]=[CH:7][C:6]([O:9][CH2:10][CH2:11][O:12][CH:13]([CH3:15])[CH3:14])=[CH:5][CH:4]=1.Br[C:19]1[CH:20]=[CH:21][C:22]2[N:28]([C:29]([O:31][C:32]([CH3:35])([CH3:34])[CH3:33])=[O:30])[CH2:27][CH2:26][C:25]([C:36]([O:38][CH3:39])=[O:37])=[CH:24][C:23]=2[CH:40]=1.C(=O)([O-])[O-].[K+].[K+]>C1(C)C=CC=CC=1.C(O)C.O.C(OCC)(=O)C.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>[C:32]([O:31][C:29]([N:28]1[C:22]2[CH:21]=[CH:20][C:19]([C:3]3[CH:8]=[CH:7][C:6]([O:9][CH2:10][CH2:11][O:12][CH:13]([CH3:15])[CH3:14])=[CH:5][CH:4]=3)=[CH:40][C:23]=2[CH:24]=[C:25]([C:36]([O:38][CH3:39])=[O:37])[CH2:26][CH2:27]1)=[O:30])([CH3:35])([CH3:34])[CH3:33]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

7

Reactant 3

HCID 11430Potassium CarbonateHCID 22329270HCID 22329270, compoundHCID 86756825HCID 86756825, compound

Product 1

HCID 22329202HCID 22329202, compoundYield 93.2%

Reagents, catalysts & solvents 3

HCID 178418397HCID 178418397, compound
Catalyst
HCID 8857Ethyl AcetateSolvent
HCID 86587398Ethanol toluene waterSolvent

Procedure

In a mixture of water ethanol toluene (1:1:10, v/v, 42.0 ml) were dissolved 4-(2-propoxy)ethoxyphenyl borate (920 mg) and methyl 7-bromo-1-(t-butoxycarbonyl)-2,3-dihydro-1H-1-benzazepine-4-carboxylate (1308 mg). To the solution was added potassium carbonate (1135 mg), and the mixture was stirred under argon atmosphere at room temperature for 30 minutes. To the mixture was added tetrakistriphenylphosphinepalladium (119 mg), and the mixture was heated to reflux under argon atmosphere for 14.5 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 (50 g, hexane:ethyl acetate=9:1→3:1) to give methyl 1-(t-butoxycarbonyl)-7-[4-(2-propoxy)ethoxyphenyl]-2.3-dihydro-1H-1-benzazepine-4-carboxylate (1536 mg, 93%) as colorless oil.

Workup

  1. temperaturethe mixture was heated
  2. temperatureto reflux under argon atmosphere for 14.5 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 (50 g, hexane:ethyl acetate=9:1→3:1)

Sources & evidence

ORD record
ord-8a44390e3d274c4ebbda253c6f4c6630
Source dataset
uspto-grants-2005_08
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US06936602B1

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes