Dichloromethane → 6-Phenyl-3-pyridineacetonitrile

HRID 1423309Notes

Reaction equation

HRID 1423309 reaction equation
[C:1]1(B(O)O)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[O-]P([O-])([O-])=O.[K+].[K+].[K+].C(Cl)Cl.Cl[C:22]1[N:27]=[CH:26][C:25]([CH2:28][C:29]#[N:30])=[CH:24][CH:23]=1>O1CCOCC1.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]>[C:1]1([C:22]2[N:27]=[CH:26][C:25]([CH2:28][C:29]#[N:30])=[CH:24][CH:23]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

8

Reactant 4

HCID 6344DichloromethaneHCID 62657Potassium Phosphate, TribasicHCID 66827Phenylboronic AcidHCID 14751282-(6-Chloropyridin-3-yl)acetonitrile

Product 1

HCID 669801836-Phenyl-3-pyridineacetonitrile

Reagents, catalysts & solvents 3

HCID 178418228Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)CatalystHCID 962WaterSolvent2×HCID 312751,4-DioxaneSolvent

Conditions

Temperature
75 °C

Procedure

Phenylboronic acid (4630.9 mg, 37.98 mmol), K3PO4 (20129 mg, 94.95 mmol), and PdCl2(dppf).CH2Cl2 (1291 mg, 1.58 mmol) was added to a solution of 2-(6-chloropyridin-3-yl)acetonitrile (5000 mg, 31.65 mmol) in dioxane (100 mL) and H2O (10 mL). The resulting mixture was stirred at 75° C. under argon overnight. The mixture was diluted with H2O and then extracted with ethyl acetate (×2). The combined organic layers were washed with brine and dried with Na2SO4. Evaporation and purification by column chromatography afforded 2-(6-phenylpyridin-3-yl)acetonitrile: LCMS tR=1.15 Min (5 min run, UV254nm), Mass calculated for, M+194.0, observed LC/MS m/z 195.0 (M+H).

Workup

  1. extractionextracted with ethyl acetate (×2)
  2. washThe combined organic layers were washed with brine
  3. dry with materialdried with Na2SO4
  4. customEvaporation and purification by column chromatography

Sources & evidence

ORD record
ord-f0f22dba7aa94d72b58f9ad7f03e8670
Source dataset
uspto-grants-2015_01
Patent number
US08927562B2

Reaction notes

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