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

HRID 491306

반응식

HRID 491306 반응식
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]

참가 물질

7

반응물 3

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

생성물 1

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

시약·촉매·용매 3

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)촉매HCID 178418476HCID 178418476, 화합물촉매HCID 8028Tetrahydrofuran용매

실험 절차

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+).

후처리

  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)

출처 및 근거

ORD 기록
ord-9a54c64f8dc84749a492eaffe6180b76
출처 데이터셋
uspto-grants-2009_05
특허 번호
US07531529B2

연결된 노트

불러오는 중…