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

HRID 1355663Notes

Reaction equation

HRID 1355663 reaction equation
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

Participants

7

Reactant 3

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

Product 1

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

Reagents, catalysts & solvents 3

HCID 176Acetic AcidSolventHCID 6422Trifluoroacetic acidSolventHCID 12052TriethylsilaneSolvent

Procedure

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.

Workup

  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

Sources & evidence

ORD record
ord-00c6e20df5a346d9b97711e1226989a7
Source dataset
uspto-grants-2003_07
Patent number
US06586447B1

Reaction notes

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