Sodium Carbonate → HCID 19045689, compound

HRID 1476310Notes

Reaction equation

HRID 1476310 reaction equation
Br[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[CH2:8][C:9]#[N:10].[Cl:11][C:12]1[CH:17]=[CH:16][C:15](B(O)O)=[CH:14][CH:13]=1.C([O-])([O-])=O.[Na+].[Na+]>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.C1(C)C=CC=CC=1>[Cl:11][C:12]1[CH:17]=[CH:16][C:15]([C:2]2[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=2[CH2:8][C:9]#[N:10])=[CH:14][CH:13]=1

Participants

6

Reactant 3

HCID 10340Sodium CarbonateHCID 296252-Bromobenzyl cyanideHCID 742994-Chlorophenylboronic acid

Product 1

HCID 19045689HCID 19045689, compoundYield 94%

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 1140TolueneSolvent

Procedure

2-(2-bromophenyl)acetonitrile (5.00 g, 25.5 mmol), 4-chlorophenylboronic acid (4.30 g, 27.5 mmol), and tetrakis(triphenylphosphine)palladium(0) (0.48 g 0.42 mmol) were mixed with toluene (57 ml) in a 250 ml 3-necked flask. A reflux condenser was attached and the flask was purged with nitrogen. Aqueous solution of Na2CO3 (2M, 29 ml, 58 mmol) was added by syringe, and the atmosphere was evacuated and replaced with nitrogen. The reaction mixture was heated at reflux overnight, and then allowed to cool at ambient temperature. The mixture was partitioned between saturated aq. NH4Cl and EtOAc (200 ml each). The organic phase was separated, dried (MgSO4), filtered through diatomaceous earth and the filtrate was evaporated under reduced pressure. The residue was purified by column chromatography (ISCO, 120 g silica gel column, 0→20% EtOAc/hexanes) to give the tile compound (5.44 g, yield: 94%).

Workup

  1. customA reflux condenser was attached
  2. customthe flask was purged with nitrogen
  3. customthe atmosphere was evacuated
  4. temperatureThe reaction mixture was heated
  5. temperatureat reflux overnight
  6. customThe mixture was partitioned between saturated aq. NH4Cl and EtOAc (200 ml each)
  7. customThe organic phase was separated
  8. dry with materialdried (MgSO4)
  9. filtrationfiltered through diatomaceous earth
  10. customthe filtrate was evaporated under reduced pressure
  11. customThe residue was purified by column chromatography (ISCO, 120 g silica gel column, 0→20% EtOAc/hexanes)

Sources & evidence

ORD record
ord-ca6ac5f355b943aab779c36bec8523f7
Source dataset
uspto-grants-2015_04
Patent number
US09018381B2

Reaction notes

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