4-Methoxycarbonylphenylboronic acid → HCID 22616369, compound

HRID 843114Notes

Reaction equation

HRID 843114 reaction equation
Br[C:2]1[CH:3]=[CH:4][C:5]2[CH2:11][CH2:10][CH2:9][C:8]([C:12]([NH:14][C:15]3[CH:20]=[CH:19][C:18]([CH2:21][N:22]([CH3:29])[CH:23]4[CH2:28][CH2:27][O:26][CH2:25][CH2:24]4)=[CH:17][CH:16]=3)=[O:13])=[CH:7][C:6]=2[CH:30]=1.[CH3:31][O:32][C:33]([C:35]1[CH:40]=[CH:39][C:38](B(O)O)=[CH:37][CH:36]=1)=[O:34]>C(=O)([O-])[O-].[K+].[K+].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>[CH3:31][O:32][C:33]([C:35]1[CH:40]=[CH:39][C:38]([C:2]2[CH:30]=[CH:6][C:5]3[CH2:11][CH2:10][CH2:9][C:8]([C:12]([NH:14][C:15]4[CH:20]=[CH:19][C:18]([CH2:21][N:22]([CH3:29])[CH:23]5[CH2:28][CH2:27][O:26][CH2:25][CH2:24]5)=[CH:17][CH:16]=4)=[O:13])=[CH:7][C:4]=3[CH:3]=2)=[CH:37][CH:36]=1)=[O:34]

Participants

7

Reactant 2

HCID 27343694-Methoxycarbonylphenylboronic acidHCID 15480020HCID 15480020, compound

Product 1

HCID 22616369HCID 22616369, compoundYield 37.7%

Reagents, catalysts & solvents 4

HCID 178418397HCID 178418397, compoundCatalystHCID 702EthanolSolventHCID 1140TolueneSolventHCID 11430Potassium CarbonateSolvent

Procedure

A mixture of 2-bromo-N-[4-[[N-methyl-N-(tetrahydropyran-4-yl)amino]methyl]phenyl]-6,7-dihydro-5H-benzocyclohepten-8-carboxamide (0.95 g) and 4-methoxycarbonylphenylboronic acid (0.4 g) in 1M potassium carbonate (6 ml), ethanol (6 ml) and toluene (75 ml) was stirred for 30 minutes at room temperature under argon. Tetrakis(triphenylphosphine)palladium (0.12 g) was added to the mixture, and the mixture was refluxed for 6 hours under argon. The reaction mixture was extracted with ethyl acetate. The organic layer was washed with water and brine, and dried over MgSO4. The solvent was evaporated in vacuo. The residue was subjected to a silica gel column chromatography (ethyl acetate/methanol/triethylamine) to give 2-(4-methoxycarbonylphenyl)-N-[4-[[N-methyl-N-(tetrahydropyran-4-yl)amino]methyl]phenyl]-6,7-dihydro-5H-benzocyclohepten-8-carboxamide (0.4 g) as colorless prisms.

Workup

  1. temperaturethe mixture was refluxed for 6 hours under argon
  2. extractionThe reaction mixture was extracted with ethyl acetate
  3. washThe organic layer was washed with water and brine
  4. dry with materialdried over MgSO4
  5. customThe solvent was evaporated in vacuo

Sources & evidence

ORD record
ord-33d5e36cc83146d4b12bb653a1f679b8
Source dataset
uspto-grants-2002_04
Patent number
US06376536B1

Reaction notes

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