Potassium Carbonate → 2-(2'-Chloro-3'-formyl-2,4'-bipyridin-6-yl)-2-methylpropanenitrile

HRID 384049Notes

Reaction equation

HRID 384049 reaction equation
[Cl:1][C:2]1[N:9]=[CH:8][CH:7]=[C:6](I)[C:3]=1[CH:4]=[O:5].[CH3:11][C:12]([C:16]1[CH:21]=[CH:20][CH:19]=[C:18](B2OCCN(C3C=CC=CC=3)CCO2)[N:17]=1)([CH3:15])[C:13]#[N:14].C1(C)C=CC=CC=1P(C1C=CC=CC=1C)C1C=CC=CC=1C.C(=O)([O-])[O-].[K+].[K+]>O1CCCC1.C([O-])(=O)C.[Pd+2].C([O-])(=O)C.[Cu]I>[Cl:1][C:2]1[C:3]([CH:4]=[O:5])=[C:6]([C:18]2[CH:19]=[CH:20][CH:21]=[C:16]([C:12]([CH3:15])([CH3:11])[C:13]#[N:14])[N:17]=2)[CH:7]=[CH:8][N:9]=1

Participants

8

Reactant 4

HCID 11430Potassium CarbonateHCID 80271Tri-o-tolylphosphineHCID 100386372-Chloro-4-iodopyridine-3-carbaldehydeHCID 579696312-Methyl-2-(6-(6-phenyl-1,3,6,2-dioxazaborocan-2-yl)pyridin-2-yl)propanenitrile

Product 1

HCID 579697572-(2'-Chloro-3'-formyl-2,4'-bipyridin-6-yl)-2-methylpropanenitrileYield 74%

Reagents, catalysts & solvents 3

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 167845palladium(II) acetateCatalystHCID 8028TetrahydrofuranSolvent

Procedure

A suspension of 2-chloro-4-iodonicotinaldehyde (90.3 mg, 0.338 mmol)(prepared via J. Org. Chem., 1993, 58, 7832), 2-methyl-2-(6-(6-phenyl-1,3,6,2-dioxazaborocan-2-yl)pyridin-2-yl)propanenitrile (226 mg, 0.675 mmol), tri-o-tolylphosphine (21 mg, 0.068 mmol), palladium acetate (5 mol %, 3.8 mg, 0.017 mmol), potassium carbonate (93 mg, 0.675 mmol) and copper(I) iodide (26 mg, 0.135 mmol) in tetrahydrofuran (5 ml) was heated at reflux under nitrogen for 75 minutes. The mixture was cooled down to room temperature, filtered through a path of celite and evaporated to dryness. The residue was purified on silica gel by flash column chromatography to afford the title compound as an off-white solid (71 mg, 74% yield).

Workup

  1. temperaturewas heated
  2. temperatureat reflux under nitrogen for 75 minutes
  3. filtrationfiltered through a path of celite
  4. customevaporated to dryness
  5. customThe residue was purified on silica gel by flash column chromatography

Sources & evidence

ORD record
ord-346971f1295c45ecb7a17e11e73593cb
Source dataset
uspto-grants-2013_02
Patent number
US08367697B2

Reaction notes

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