Hydrogen Peroxide → 3-(4-Cyanophenyl)-2,6-dimethyl-4-(phenylmethoxy)pyridine

HRID 654374Notes

Reaction equation

HRID 654374 reaction equation
C(C1[CH:12]=[C:11](OCC2C=CC(B(O)O)=CC=2)[C:10]2[CH2:9][CH2:8]CC[C:5]=2[N:4]=1)C.[CH2:24]([C:26]1[C:31]([C:32](OC)=O)=[C:30]([O:36][CH2:37][C:38]2[CH:47]=[CH:46][C:41](C(OC)=O)=[CH:40][CH:39]=2)[CH:29]=[C:28]([CH2:48]C)[N:27]=1)C.C(=O)([O-])O.[Na+].OO>CO.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>[C:5]([C:10]1[CH:11]=[CH:12][C:32]([C:31]2[C:26]([CH3:24])=[N:27][C:28]([CH3:48])=[CH:29][C:30]=2[O:36][CH2:37][C:38]2[CH:39]=[CH:40][CH:41]=[CH:46][CH:47]=2)=[CH:8][CH:9]=1)#[N:4]

Participants

8

Reactant 4

HCID 784Hydrogen PeroxideHCID 516892Sodium BicarbonateHCID 151714224-[(2-Ethyl-5,6,7,8-tetrahydroquinolin-4-yl)oxymethyl]phenylboronic acidHCID 15171426Methyl 4-[(2,6-diethyl-3-methoxycarbonylpyridin-4-yloxy)methyl]benzoate

Product 1

HCID 151714353-(4-Cyanophenyl)-2,6-dimethyl-4-(phenylmethoxy)pyridine

Reagents, catalysts & solvents 3

HCID 178418397HCID 178418397, compoundCatalystHCID 887MethanolSolventHCID 1140TolueneSolvent

Procedure

A solution of compound C (188 mg) in methanol (1 ml) was added to a mixture of compound B (170 mg), tetrakis(triphenylphosphine)palladium (30 mg), 2M sodium hydrogen carbonate solution (2 ml) and toluene (10 ml). The mixture was heated under reflux for 12 hours and then allowed to cool. Hydrogen peroxide solution (30 wt. % solution in water; 0.1 ml) was added and the mixture was stirred for 30 minutes. The aqueous phase was separated and extracted with ethyl acetate (2×25 ml). The combined organic solutions were dried (MgSO4) and volatile material was removed by evaporation. The residue was purified by flash chromatography, eluting with ethyl acetate/hexane (4:1 v/v) to give 3-(4-cyanophenyl)-2,6-dimethyl-4-(phenylmethoxy)pyridine (D), as a gum; NMR (CDCl3): 2.3(s,3H), 2.6(s,3H), 5.1(s,2H), 6.7(s,1H), 7.1-7.2(m,2H), 7.25-7.35(m,5H), 7.7(d,2H).

Workup

  1. temperatureThe mixture was heated
  2. temperatureunder reflux for 12 hours
  3. temperatureto cool
  4. customThe aqueous phase was separated
  5. extractionextracted with ethyl acetate (2×25 ml)
  6. dry with materialThe combined organic solutions were dried (MgSO4) and volatile material
  7. customwas removed by evaporation
  8. customThe residue was purified by flash chromatography
  9. washeluting with ethyl acetate/hexane (4:1 v/v)

Sources & evidence

ORD record
ord-10f78fcd10884dc2a21ec1d8057c0a33
Source dataset
uspto-grants-1992_07
Patent number
US05130318

Reaction notes

Loading…