Water → HCID 68106705, compound

HRID 2403619Notes

Reaction equation

HRID 2403619 reaction equation
Br[C:2]1[CH:3]=[C:4]([CH:19]=[CH:20][CH:21]=1)[CH2:5][N:6]([CH3:18])[C:7](=[O:17])[CH2:8][NH:9]C(=O)OC(C)(C)C.O.[Cl:23][C:24]1[CH:29]=[CH:28][C:27](B(O)O)=[CH:26][CH:25]=1.C(=O)([O-])[O-].[Na+].[Na+]>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>[ClH:23].[Cl:23][C:24]1[CH:29]=[CH:28][C:27]([C:2]2[CH:21]=[CH:20][CH:19]=[C:4]([CH2:5][N:6]([CH3:18])[C:7](=[O:17])[CH2:8][NH2:9])[CH:3]=2)=[CH:26][CH:25]=1

Participants

7

Reactant 4

HCID 962Water2×HCID 10340Sodium CarbonateHCID 742994-Chlorophenylboronic acidHCID 70570939HCID 70570939, compound

Product 1

HCID 68106705HCID 68106705, compoundYield 133.7%

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 1140TolueneSolvent

Conditions

Temperature
80 °C

Procedure

To a suspension of tert-butyl {2-[(3-bromobenzyl)(methyl)amino]-2-oxoethyl}carbamate (293 mg) in toluene (4 ml) were added water (2 ml), (4-chlorophenyl)boronic acid (192 mg), sodium carbonate (173 mg), and tetrakis(triphenylphosphine)palladium (28 mg), followed by stirring at 80° C. overnight. The reaction mixture was cooled to room temperature, and then water was added thereto, followed by extraction with EtOAc. The organic layer was concentrated under reduced pressure, and then the residue was purified by silica gel column chromatography (hexane/EtOAc=10/0 to ½). The purified product was dissolved in EtOAc (5 ml), and then 4 M hydrogen chloride/EtOAc (10 ml) was added thereto, followed by stirring at room temperature for 2 hours. The reaction mixture was concentrated under reduced pressure, and then MeCN was added thereto. The precipitated solid was collected and washed with MeCN to obtain N-[(4′-chlorobiphenyl-3-yl)methyl]-N-methylglycinamide hydrochloride (267 mg).

Workup

  1. temperatureThe reaction mixture was cooled to room temperature
  2. extractionfollowed by extraction with EtOAc
  3. concentrationThe organic layer was concentrated under reduced pressure
  4. customthe residue was purified by silica gel column chromatography (hexane/EtOAc=10/0 to ½)
  5. dissolutionThe purified product was dissolved in EtOAc (5 ml)
  6. addition4 M hydrogen chloride/EtOAc (10 ml) was added
  7. stirringby stirring at room temperature for 2 hours
  8. concentrationThe reaction mixture was concentrated under reduced pressure
  9. additionMeCN was added
  10. customThe precipitated solid was collected
  11. washwashed with MeCN

Sources & evidence

ORD record
ord-3b79bb0e624d42af8f2ca19a72a43951
Source dataset
uspto-grants-2014_08
Patent number
US08802679B2

Reaction notes

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