3-Chloro-6-phenylpyridazine → 4-(6-Phenylpyridazin-3-yl)-1,4-diazatricyclo[4.3.1.13,8]undecane

HRID 80418

반응식

HRID 80418 반응식
Cl[C:2]1[N:3]=[N:4][C:5]([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)=[CH:6][CH:7]=1.[Cl-].C(C1C=CC=C(C(C)C)C=1[N+:27]1[CH:31]=[CH:30][N:29]([C:32]2[C:37]([CH:38](C)C)=[CH:36][CH:35]=[CH:34]C=2C(C)C)[CH:28]=1)(C)C.CC(C)([O-])C.[Na+]>C1(C)C=CC=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd]>[C:8]1([C:5]2[N:4]=[N:3][C:2]([N:27]3[CH2:38][CH:37]4[CH2:32][N:29]5[CH2:28][CH:35]([CH2:34][CH:31]3[CH2:30]5)[CH2:36]4)=[CH:7][CH:6]=2)[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1

참가 물질

6

반응물 3

HCID 885153-Chloro-6-phenylpyridazineHCID 27349131,3-Bis(2,6-diisopropylphenyl)imidazolium chlorideHCID 23676156Sodium t-butoxide

생성물 1

HCID 498707764-(6-Phenylpyridazin-3-yl)-1,4-diazatricyclo[4.3.1.13,8]undecane

시약·촉매·용매 2

HCID 9811564Bis(dibenzylideneacetone)palladium촉매HCID 1140Toluene용매

반응 조건

온도
90 °C

실험 절차

A solution of the product of Example 2 (0.10 g, 0.66 mmol) in dry toluene (10 mL) was treated with 3-chloro-6-phenylpyridazine (0.20 g, 1.0 mmol; Aldrich), tris(dibenzylideneacetone)dipalladium(0) (Pd2(dba)3; 0.01 g, 0.013 mmol; Alfa Aesar), 1,3-bis(2,6-di-iso-propylphenyl)imidazolium chloride (0.017 g, 0.04 mmol; Strem), and sodium tert-butoxide (0.148 g, 1.32 mmol). The mixture was purged with nitrogen and heated to 90° C. for 8 hours. After cooling to room temperature, the reaction was quenched by pouring into a 5% aqueous NaHCO3 solution. The mixture was extracted with chloroform (3×), washed with brine, dried (MgSO4), filtered and concentrated. The crude product was purified by flash chromatography on silica gel, eluting with 2-10% methanol (containing 1% ammonium hydroxide)-chloroform to afford the title compound: MS (DCI/NH3) m/z 307 (M+H)+.

후처리

  1. customThe mixture was purged with nitrogen
  2. temperatureAfter cooling to room temperature
  3. customthe reaction was quenched
  4. additionby pouring into a 5% aqueous NaHCO3 solution
  5. extractionThe mixture was extracted with chloroform (3×)
  6. washwashed with brine
  7. dry with materialdried (MgSO4)
  8. filtrationfiltered
  9. concentrationconcentrated
  10. customThe crude product was purified by flash chromatography on silica gel
  11. washeluting with 2-10% methanol (containing 1% ammonium hydroxide)-chloroform

출처 및 근거

ORD 기록
ord-ac62a457a9a341128a0cf870cc90b89f
출처 데이터셋
uspto-grants-2014_09
특허 번호
US08846661B2

연결된 노트

불러오는 중…