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

HRID 1920837ノート

反応式

HRID 1920837 の反応式
[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

参加物

8

反応物 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

生成物 1

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

試薬・触媒・溶媒 3

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)触媒HCID 167845palladium(II) acetate触媒HCID 8028Tetrahydrofuran溶媒

実験手順

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).

後処理

  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

出典と根拠

ORDレコード
ord-33a1357196754780ae0f0cc191012309
出典データセット
uspto-grants-2012_05
特許番号
US08173635B2

反応ノート

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