Benzyl Bromide → HCID 24829235, compound

HRID 883648Notes

Reaction equation

HRID 883648 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]2[C:10]3([CH2:14][C:13](=[O:15])[NH:12][C:11]3=[O:16])[C:9](=[O:17])[NH:8][C:5]2=[CH:6][CH:7]=1.CC(C)([O-])C.[K+].[CH2:24](Br)[C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1>CN(C)C=O.O>[CH2:24]([N:12]1[C:13](=[O:15])[CH2:14][C:10]2([C:4]3[C:5](=[CH:6][CH:7]=[C:2]([Cl:1])[CH:3]=3)[NH:8][C:9]2=[O:17])[C:11]1=[O:16])[C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1

Participants

6

Reactant 3

HCID 7498Benzyl BromideHCID 20279349HCID 20279349, compoundHCID 23665647Potassium tert-butoxide

Product 1

HCID 24829235HCID 24829235, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

A stirred solution of the crude 5-chloro-1H-spiro[indole-3,3′-pyrrolidine]-2,2′,5′-trione, intermediate 9 (800 mg, 3.19 mmol) in anhydrous N,N-dimethylformamide (6 ml) was treated with potassium tert-butoxide (377 mg, 3.19 mmol). After stirring at ambient temperature for 40 min, benzyl bromide (0.38 ml, 3.19 mmol) was added. The mixture was stirred for 2 hours and left to stand overnight. The resultant mixture was diluted with water (50 ml) and extracted with ethyl acetate (3×50 ml). The combined extracts were dried (MgSO4) and the solvent removed in vacuo to give the crude 1′-benzyl-5-chloro-1H-spiro[indole-3,3′-pyrrolidine]-2,2′,5′-trione which was purified by flash chromatography (silica) eluting with petroleum ether (40-60) containing an increasing amount (0 to 75%) of ethyl acetate. This gave 789 mg (73%) of a yellow solid.

Workup

  1. stirringThe mixture was stirred for 2 hours
  2. waitleft
  3. waitto stand overnight
  4. extractionextracted with ethyl acetate (3×50 ml)
  5. dry with materialThe combined extracts were dried (MgSO4)
  6. customthe solvent removed in vacuo

Sources & evidence

ORD record
ord-22f439c3d7504261a58244ddbe8b9237
Source dataset
uspto-grants-2012_08
Patent number
US08236963B2

Reaction notes

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