Triphenylphosphine → 4-[2-(Trimethylsilyl)ethynyl]pyridine-2-carbonitrile

HRID 491306

反応式

HRID 491306 の反応式
Br[C:2]1[CH:7]=[CH:6][N:5]=[C:4]([C:8]#[N:9])[CH:3]=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[CH3:29][Si:30]([C:33]#[CH:34])([CH3:32])[CH3:31]>C1COCC1.Cl[Pd](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1.[Cu]I>[CH3:29][Si:30]([C:33]#[C:34][C:2]1[CH:7]=[CH:6][N:5]=[C:4]([C:8]#[N:9])[CH:3]=1)([CH3:32])[CH3:31]

参加物

7

反応物 3

HCID 11776TriphenylphosphineHCID 66111TrimethylsilylacetyleneHCID 6932834-Bromo-2-cyanopyridine

生成物 1

HCID 451164464-[2-(Trimethylsilyl)ethynyl]pyridine-2-carbonitrile

試薬・触媒・溶媒 3

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)触媒HCID 178418476HCID 178418476、化合物触媒HCID 8028Tetrahydrofuran溶媒

実験手順

4-Bromo-2-pyridinecarbonitrile [Cesko-Slovenska Farmacie 25(5),181(1976)] (0.73 g, 4.0 mmol) was dissolved in 18 mL dry THF. This mixture was evacuated and backfilled with argon several times to remove oxygen from the solution. Triphenylphosphine (31 mg, 0.12 mmol) and bis(triphenylphosphine)palladium(II) chloride (141 mg, 0.20 mmol) were added and the reaction mixture was stirred at room temperature for 1 h. Copper(I) iodide (23 mg, 0.12 mmol) and trimethylsilyl-acetylene (590 mg, 6.0 mmol) were added. The reaction mixture was stirred at room temperature for 3 days. The solvent was evaporated. The residue was taken up in 100 mL water and extracted three times with 100 ml of ethyl acetate. The combined organic extracts were dried with magnesium sulfate, filtered and evaporated. The crude product was purified by flash chromatography on silica gel (heptane/methylene chloride 1:2). The desired product was obtained as a yellow oil (329 mg, 41%), MS: m/e=201.3 (M+H+).

後処理

  1. customThis mixture was evacuated
  2. customto remove oxygen from the solution
  3. stirringThe reaction mixture was stirred at room temperature for 3 days
  4. customThe solvent was evaporated
  5. extractionextracted three times with 100 ml of ethyl acetate
  6. dry with materialThe combined organic extracts were dried with magnesium sulfate
  7. filtrationfiltered
  8. customevaporated
  9. customThe crude product was purified by flash chromatography on silica gel (heptane/methylene chloride 1:2)

出典と根拠

ORDレコード
ord-9a54c64f8dc84749a492eaffe6180b76
出典データセット
uspto-grants-2009_05
特許番号
US07531529B2

関連ノート

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