Sodium Carbonate → [2'-(3-Methoxypropyl)-3-methylbiphenyl-4-yl]acetonitrile

HRID 2194924Notes

Reaction equation

HRID 2194924 reaction equation
Br[C:2]1[CH:7]=[CH:6][C:5]([CH2:8][C:9]#[N:10])=[C:4]([CH3:11])[CH:3]=1.[CH3:12][O:13][CH2:14][CH2:15][CH2:16][C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][C:18]=1B(O)O.C([O-])([O-])=O.[Na+].[Na+]>CN(C=O)C.O.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.Cl[Pd]Cl.[Fe+2]>[CH3:12][O:13][CH2:14][CH2:15][CH2:16][C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][C:18]=1[C:2]1[CH:7]=[CH:6][C:5]([CH2:8][C:9]#[N:10])=[C:4]([CH3:11])[CH:3]=1

Participants

7

Reactant 3

HCID 10340Sodium CarbonateHCID 184142962-(4-Bromo-2-methylphenyl)acetonitrileHCID 58083347[2-(3-Methoxypropyl)phenyl]boronic acid

Product 1

HCID 58083338[2'-(3-Methoxypropyl)-3-methylbiphenyl-4-yl]acetonitrile

Reagents, catalysts & solvents 3

HCID 178418228Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)CatalystHCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

To a solution of (4-bromo-2-methylphenyl)acetonitrile (1 eq.) and [2-(3-methoxypropyl)phenyl]boronic acid from EXAMPLE 3 step 1, in DMF (0.22M) was added aqueous Na2CO3 (2M; 3 eq.). Nitrogen was bubbled in the solution for 15 min before the addition of PdCl2(dppf)2 (0.05 eq.). The final mixture was stirred at 90° C. for 12 h, cooled to room temperature, poured in water and extracted with Et2O. The organic extract was washed with water, HCl (0.01M), brine, dried over MgSO4 filtered and concentrated. Purification by column chromatography on silica gel (Combi-Flash by ISCO), eluting with Hex/EtOAc (5 to 30% in 30 min) afforded the desired compound as a colorless oil.

Workup

  1. extractionextracted with Et2O
  2. extractionThe organic extract
  3. washwas washed with water, HCl (0.01M), brine
  4. dry with materialdried over MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customPurification by column chromatography on silica gel (Combi-Flash by ISCO)
  8. washeluting with Hex/EtOAc (5 to 30% in 30 min)

Sources & evidence

ORD record
ord-bea63c37d3aa47668e28e54b05e7c7be
Source dataset
uspto-grants-2012_12
Patent number
US08334308B2

Reaction notes

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