1-Naphthaldehyde → 6-Bromo-1-naphthalen-1-ylmethyl-1,3-dihydro-indol-2-one

HRID 1355663노트

반응식

HRID 1355663 반응식
C(OC(=O)[CH:7]([C:15]1[CH:20]=[CH:19][C:18]([Br:21])=[CH:17][C:16]=1[NH2:22])[C:8]([O:10]C(C)(C)C)=O)(C)(C)C.[CH:24]1[CH:29]=[C:28]2[CH:30]=[CH:31][CH:32]=[C:33]([CH:34]=O)[C:27]2=[CH:26][CH:25]=1.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>C(O)(=O)C.C(O)(C(F)(F)F)=O.C([SiH](CC)CC)C>[Br:21][C:18]1[CH:17]=[C:16]2[C:15]([CH2:7][C:8](=[O:10])[N:22]2[CH2:34][C:33]2[C:27]3[C:28](=[CH:29][CH:24]=[CH:25][CH:26]=3)[CH:30]=[CH:31][CH:32]=2)=[CH:20][CH:19]=1

참가 물질

7

반응물 3

HCID 61951-NaphthaldehydeHCID 5049666Sodium triacetoxyborohydrideHCID 700318672-(2-Amino-4-bromo-phenyl)-malonic acid di-tert-butyl ester

생성물 1

HCID 185077696-Bromo-1-naphthalen-1-ylmethyl-1,3-dihydro-indol-2-one수율 91.3%

시약·촉매·용매 3

HCID 176Acetic Acid용매HCID 6422Trifluoroacetic acid용매HCID 12052Triethylsilane용매

실험 절차

2-(2-Amino-4-bromo-phenyl)-malonic acid di-tert-butyl ester (7.73 g, 20.0 mmol) and 1-napthylaldehyde (3.0 ml, 22.0 mmol) were dissolved in 80 ml of acetic acid (AcOH) under an atmosphere of dry N2. To this solution was added 95% sodium triacetoxyborohydride (NaHB(OAc)3) (5.8 g, 26 mmol) and the solution was stirred for 45 minutes. The reaction mixture was concentrated under vacuum and then stirred in 100 ml of a 1:1 solution of DCM/water. To this mixture was slowly added NaHCO3 until the pH˜8. The DCM layer was then washed with saturated aqueous NaHCO3 and dried over MgSO4, filtered and concentrated under vacuum to give a foam which was subsequently dissolved in a solution of 80 ml of TFA and 10 ml of triethylsilane under an atmosphere of dry N2. The mixture was stirred overnight after which time the precipitate was collected, washed with hexanes and dried under vacuum to give 6.43 g of the titled compound as a white solid in 90% yield.

후처리

  1. concentrationThe reaction mixture was concentrated under vacuum
  2. stirringstirred in 100 ml of a 1:1 solution of DCM/water
  3. washThe DCM layer was then washed with saturated aqueous NaHCO3
  4. dry with materialdried over MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated under vacuum
  7. customto give a foam which
  8. stirringThe mixture was stirred overnight after which time the precipitate
  9. customwas collected
  10. washwashed with hexanes
  11. customdried under vacuum

출처 및 근거

ORD 기록
ord-00c6e20df5a346d9b97711e1226989a7
출처 데이터셋
uspto-grants-2003_07
특허 번호
US06586447B1

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