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

HRID 384049노트

반응식

HRID 384049 반응식
[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

참가 물질

8

반응물 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

생성물 1

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

시약·촉매·용매 3

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)촉매HCID 167845palladium(II) acetate촉매HCID 8028Tetrahydrofuran용매

실험 절차

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).

후처리

  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

출처 및 근거

ORD 기록
ord-346971f1295c45ecb7a17e11e73593cb
출처 데이터셋
uspto-grants-2013_02
특허 번호
US08367697B2

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