Benzophenone imine → HCID 178450079, 화합물

HRID 1368552노트

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HRID 1368552 반응식
Br[C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[CH:8]=[C:7]([C:12]([C:17]1[N:18]=[CH:19][N:20](C(C3C=CC=CC=3)(C3C=CC=CC=3)C3C=CC=CC=3)[CH:21]=1)([OH:16])[CH:13]([CH3:15])[CH3:14])[CH:6]=[CH:5]2.C(=[NH:54])(C1C=CC=CC=1)C1C=CC=CC=1.CC(C)([O-])C.[Na+]>C1(C)C=CC=CC=1.C(OCC)(=O)C.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].C1C=CC(P(C2C=CC3C(=CC=CC=3)C=2C2C3C(=CC=CC=3)C=CC=2P(C2C=CC=CC=2)C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[NH2:54][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[CH:8]=[C:7]([C:12]([C:17]1[N:18]=[CH:19][NH:20][CH:21]=1)([OH:16])[CH:13]([CH3:15])[CH3:14])[CH:6]=[CH:5]2

참가 물질

8

반응물 3

HCID 136809Benzophenone imineHCID 22018349HCID 22018349, 화합물HCID 23676156Sodium t-butoxide

생성물 1

HCID 178450079HCID 178450079, 화합물수율 213.3%

시약·촉매·용매 4

HCID 634876Binap, (A+-)-촉매HCID 9811564Bis(dibenzylideneacetone)palladium촉매HCID 1140Toluene용매HCID 8857Ethyl Acetate용매

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온도
80 °C

실험 절차

1-(6-Bromonaphthalen-2-yl)-2-methyl-1-(1-trityl-1H-imidazol-4-yl)-1-propanol (14.0 g), benzophenonimine (5.18 g), tris(dibenzylideneacetone)dipalladium (440 mg), (R)-(+)-2,2′-bis(diphenylphosphino)-1,1′-binaphthyl (872 mg) and sodium t-butoxide (5.72 g) were dissolved in toluene (140 ml). The solution was stirred at 80° C. for 18 h under argon atmosphere. The solution was cooled, and diluted with ethyl acetate. The mixture was filtered with celite, the residue was washed with ethyl acetate. The filtrate was concentrated and the residue was purified by silica gel chromatography (eluent, hexane:THF=1:1), then recrystallized from hexane-THF (4:1) to give the titled compound (14.3 g) as a yellow powder.

후처리

  1. temperatureThe solution was cooled
  2. filtrationThe mixture was filtered with celite
  3. washthe residue was washed with ethyl acetate
  4. concentrationThe filtrate was concentrated
  5. customthe residue was purified by silica gel chromatography (eluent, hexane:THF=1:1)
  6. customrecrystallized from hexane-THF (4:1)

출처 및 근거

ORD 기록
ord-865ea257d4d34e628c376fa0914bbfd0
출처 데이터셋
uspto-grants-2003_06
특허 번호
US06573289B1

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