Benzophenone imine → N-(diphenylmethylidene)-3-[1-(4-methoxybenzyl)-4-pyridin-4-yl-1H-pyrazol-3-yl]aniline

HRID 1843623노트

반응식

HRID 1843623 반응식
Br[C:2]1[CH:3]=[C:4]([C:8]2[C:12]([C:13]3[CH:18]=[CH:17][N:16]=[CH:15][CH:14]=3)=[CH:11][N:10]([CH2:19][C:20]3[CH:25]=[CH:24][C:23]([O:26][CH3:27])=[CH:22][CH:21]=3)[N:9]=2)[CH:5]=[CH:6][CH:7]=1.C1(P(C2C=CC=CC=2)C2C=CC3C(=CC=CC=3)C=2C2C3C(=CC=CC=3)C=CC=2P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.CC(C)([O-])C.[Na+].[C:80](=[NH:93])([C:87]1[CH:92]=[CH:91][CH:90]=[CH:89][CH:88]=1)[C:81]1[CH:86]=[CH:85][CH:84]=[CH:83][CH:82]=1>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:87]1([C:80]([C:81]2[CH:82]=[CH:83][CH:84]=[CH:85][CH:86]=2)=[N:93][C:2]2[CH:7]=[CH:6][CH:5]=[C:4]([C:8]3[C:12]([C:13]4[CH:18]=[CH:17][N:16]=[CH:15][CH:14]=4)=[CH:11][N:10]([CH2:19][C:20]4[CH:25]=[CH:24][C:23]([O:26][CH3:27])=[CH:22][CH:21]=4)[N:9]=3)[CH:3]=2)[CH:88]=[CH:89][CH:90]=[CH:91][CH:92]=1

참가 물질

7

반응물 4

HCID 136809Benzophenone imineHCID 634876Binap, (A+-)-HCID 23676156Sodium t-butoxideHCID 671844264-[3-(3-bromophenyl)-1-(4-methoxybenzyl)-1H-pyrazol-4-yl]pyridine

생성물 1

HCID 86654334N-(diphenylmethylidene)-3-[1-(4-methoxybenzyl)-4-pyridin-4-yl-1H-pyrazol-3-yl]aniline수율 65%

시약·촉매·용매 2

HCID 9811564Bis(dibenzylideneacetone)palladium촉매HCID 1140Toluene용매

실험 절차

1.9 g (4.5 mmol) of 4-[3-(3-bromophenyl)-1-(4-methoxybenzyl)-1H-pyrazol-4-yl]pyridine were dissolved in 60 ml of dry toluene under nitrogen atmosphere and 366 mg (0.4 mmol) of tris(dibenzylidene-acetone)dipalladium(0), 498 mg (0.8 mmol) of racemic 2,2′-bis(diphenylphosphino)-1,1′-binaphtalene, 562 mg (5.85 mmol) of sodium tertbutoxide and 975 L (5.85 mmol) of benzophenonimine were added to the solution successively. The mixture was refluxed for 3 hours. After cooling to room temperature the reaction mixture was filtered over a celite pad and the solvent evaporated. The residue was redissolved with ethylacetate and washed with water. The organic layer was dried over Na2SO4 and evaporated again to dryness. The crude was purified by chromatography on a silica gel column eluted by dichloromethane-methanol 95/5, affording 1.5 g (65% yield) of the title compound.

후처리

  1. temperatureThe mixture was refluxed for 3 hours
  2. filtrationwas filtered over a celite pad
  3. customthe solvent evaporated
  4. dissolutionThe residue was redissolved with ethylacetate
  5. washwashed with water
  6. dry with materialThe organic layer was dried over Na2SO4
  7. customevaporated again to dryness
  8. customThe crude was purified by chromatography on a silica gel column
  9. washeluted by dichloromethane-methanol 95/5

출처 및 근거

ORD 기록
ord-dcbf87829c8c494d9ea6c5d37b8b8645
출처 데이터셋
uspto-grants-2015_02
특허 번호
US08946250B2

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