Methyltriphenylphosphonium iodide → 4-(4-Benzyl-phthalazin-1-yl)-5'-isopropenyl-3,4,5,6-tetrahydro-2H-[1,2']bipyrazinyl

HRID 42194

반응식

HRID 42194 반응식
[I-].[CH3:2][P+](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1.CC(C)([O-])C.[K+].[CH2:28]([C:35]1[C:44]2[C:39](=[CH:40][CH:41]=[CH:42][CH:43]=2)[C:38]([N:45]2[CH2:50][CH2:49][N:48]([C:51]3[CH:56]=[N:55][C:54]([C:57](=O)[CH3:58])=[CH:53][N:52]=3)[CH2:47][CH2:46]2)=[N:37][N:36]=1)[C:29]1[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=1>C1COCC1>[CH2:28]([C:35]1[C:44]2[C:39](=[CH:40][CH:41]=[CH:42][CH:43]=2)[C:38]([N:45]2[CH2:50][CH2:49][N:48]([C:51]3[CH:56]=[N:55][C:54]([C:57]([CH3:58])=[CH2:2])=[CH:53][N:52]=3)[CH2:47][CH2:46]2)=[N:37][N:36]=1)[C:29]1[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=1

참가 물질

5

반응물 3

HCID 638159Methyltriphenylphosphonium iodide2회HCID 23665647Potassium tert-butoxide2회HCID 592406321-[4-(4-Benzyl-phthalazin-1-yl)-3,4,5,6-tetrahydro-2H-[1,2]bipyrazinyl-5'-yl]-ethanone

생성물 1

HCID 592405284-(4-Benzyl-phthalazin-1-yl)-5'-isopropenyl-3,4,5,6-tetrahydro-2H-[1,2']bipyrazinyl수율 78.9%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매3회

반응 조건

온도
5 °C

실험 절차

Methyltriphenylphosphonium iodide (115 mg, 0.28 mmol) is dissolved in THF (750 μL) and chilled to 5° C. While stirring add potassium t-butoxide (310 μL, 1M in THF, 0.31 mmol) to the solution. After 30 minutes add the mixture to a solution of 1-[4-(4-Benzyl-phthalazin-1-yl)-3,4,5,6-tetrahydro-2H-[1,2]bipyrazinyl-5′-yl]-ethanone (100 mg, 0.24 mmol) and THF (750 μL). Stir 30 minutes. Analysis shows 60-70% completion. A second portion of methyl triphenyl phosphonium iodide (115 mg, 0.28 mmol) is dissolved in THF (750 μl) and chilled to 5° C. While stirring add potassium t-butoxide (310 μL, 1M in THF, 0.31 mmol) to the solution. Again add this mixture to the current reaction. Reaction quickly proceeds to completion. Quench by adding saturated ammonium chloride. Concentrate in vacuo to remove THF and partition between water and EtOAc. Extract with EtOAc, and wash combined organics with brine. Concentrate EtOAc in vacuo. The residue is purified by flash chromatography on silica gel (EtOAc/Heptane) to afford the title compound (80 mg, 78%).

후처리

  1. stirringStir 30 minutes
  2. temperaturechilled to 5° C
  3. stirringWhile stirring
  4. additionAgain add this mixture
  5. customto the current reaction
  6. customReaction
  7. customQuench
  8. additionby adding saturated ammonium chloride
  9. concentrationConcentrate in vacuo
  10. customto remove THF
  11. custompartition between water and EtOAc
  12. extractionExtract with EtOAc
  13. washwash
  14. customThe residue is purified by flash chromatography on silica gel (EtOAc/Heptane)

출처 및 근거

ORD 기록
ord-ea71cd983c34410085938ee95ef21ee6
출처 데이터셋
uspto-grants-2013_09
특허 번호
US08536168B2

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