Water → HCID 131728111, compound

HRID 2235049Notes

Reaction equation

HRID 2235049 reaction equation
[C:1]([O:5][C:6](=[O:21])[NH:7][CH:8]1[CH2:12][C:11](=[O:13])[N:10]([C:14]2[CH:19]=[CH:18][C:17](Br)=[CH:16][CH:15]=2)[CH2:9]1)([CH3:4])([CH3:3])[CH3:2].O.[CH3:23][N:24]([CH2:26][C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][C:28]=1B(O)O)[CH3:25].C(=O)([O-])[O-].[K+].[K+]>C1(C)C=CC=CC=1.[Br-].C([N+](CCCC)(CCCC)CCCC)CCC.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:1]([O:5][C:6](=[O:21])[NH:7][CH:8]1[CH2:12][C:11](=[O:13])[N:10]([C:14]2[CH:19]=[CH:18][C:17]([C:29]3[CH:30]=[CH:31][CH:32]=[C:27]([CH2:26][N:24]([CH3:25])[CH3:23])[CH:28]=3)=[CH:16][CH:15]=2)[CH2:9]1)([CH3:4])([CH3:3])[CH3:2]

Participants

8

Reactant 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 2734345{2-[(Dimethylamino)methyl]phenyl}boronic acid2×HCID 117893471HCID 117893471, compound

Product 1

HCID 131728111HCID 131728111, compound

Reagents, catalysts & solvents 3

HCID 74236Tetrabutylammonium BromideCatalystHCID 178418397HCID 178418397, compoundCatalystHCID 1140TolueneSolvent

Procedure

525 mg (1.48 mmol) tert-butyl[1-(4-bromo-phenyl)-5-oxo-pyrrolidin-3-yl]-carbamate are dissolved in 30 ml of toluene and 5 ml of water and combined with 318 mg (1.77 mmol) 2-(N,N-dimethylaminomethyl)phenylboronic acid, 48 mg (0.15 mmol) tetrabutylammonium bromide and 314 mg (2.96 mmol) potassium carbonate, and lastly 173 mg (0.15 mmol) tetrakis(triphenylphosphine)palladium(0) are added. The reaction solution is refluxed for 90 minutes at 400 Watt in the microwave. Then another 330 mg (1.84 mmol) 2-(N,N-dimethylaminomethyl)phenylboronic acid are added and the mixture is heated for one hour at 400 Watt in the microwave. The reaction solution is evaporated to dryness i. vac. The residue is purified by reversed phase chromatography.

Workup

  1. additionare added
  2. temperatureThe reaction solution is refluxed for 90 minutes at 400 Watt in the microwave
  3. temperaturethe mixture is heated for one hour at 400 Watt in the microwave
  4. customThe reaction solution is evaporated to dryness i
  5. customThe residue is purified by reversed phase chromatography

Sources & evidence

ORD record
ord-5645a5ae441341af99b512bf3f338c29
Source dataset
uspto-grants-2010_05
Patent number
US07714000B2

Reaction notes

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