Sodium Iodide → Tert-butyl 3-((4-oxo-8-(3-(2-oxoindolin-3-yl)propyl)-1-phenyl-1,3,8-triazaspiro[4.5]decan-3-yl)methyl)benzoate

HRID 2363028Notes

Reaction equation

HRID 2363028 reaction equation
[O:1]=[C:2]1[C:6]2([CH2:11][CH2:10][NH:9][CH2:8][CH2:7]2)[N:5]([C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)[CH2:4][N:3]1[CH2:18][C:19]1[CH:20]=[C:21]([CH:29]=[CH:30][CH:31]=1)[C:22]([O:24][C:25]([CH3:28])([CH3:27])[CH3:26])=[O:23].CS(O[CH2:37][CH2:38][CH2:39][CH:40]1[C:48]2[C:43](=[CH:44][CH:45]=[CH:46][CH:47]=2)[NH:42][C:41]1=[O:49])(=O)=O.[I-].[Na+].C(=O)([O-])[O-].[K+].[K+]>CC(=O)CC.C(OCC)(=O)C>[O:1]=[C:2]1[C:6]2([CH2:11][CH2:10][N:9]([CH2:37][CH2:38][CH2:39][CH:40]3[C:48]4[C:43](=[CH:44][CH:45]=[CH:46][CH:47]=4)[NH:42][C:41]3=[O:49])[CH2:8][CH2:7]2)[N:5]([C:12]2[CH:13]=[CH:14][CH:15]=[CH:16][CH:17]=2)[CH2:4][N:3]1[CH2:18][C:19]1[CH:20]=[C:21]([CH:29]=[CH:30][CH:31]=1)[C:22]([O:24][C:25]([CH3:28])([CH3:26])[CH3:27])=[O:23]

Participants

7

Reactant 4

HCID 5238Sodium IodideHCID 11430Potassium CarbonateHCID 580466483-(2-Oxoindolin-3-yl)propyl methanesulfonateHCID 58046667Tert-butyl 3-((4-oxo-1-phenyl-1,3,8-triazaspiro[4.5]decan-3-yl)methyl)benzoate

Product 1

HCID 58046624Tert-butyl 3-((4-oxo-8-(3-(2-oxoindolin-3-yl)propyl)-1-phenyl-1,3,8-triazaspiro[4.5]decan-3-yl)methyl)benzoateYield 82.2%

Reagents, catalysts & solvents 2

HCID 6569Methyl Ethyl KetoneSolventHCID 8857Ethyl AcetateSolvent

Procedure

tert-Butyl 3-((4-oxo-1-phenyl-1,3,8-triazaspiro[4.5]decan-3-yl)methyl)benzoate (0.25 g, 0.593 mmol), 3-(2-oxoindolin-3-yl)propyl methanesulfonate (0.16 g, 0.593 mmolmmol), sodium iodide (0.027 g, 0.178 mmol) and potassium carbonate (0.12 g, 0.890 mmol) in 2-butanone (8 mL) were stirred at 78° C. for 2 hours. The reaction was diluted with ethyl acetate, washed with water and brine, dried (MgSO4), and evaporated. The residue was purified by PTLC (5% methanol/dichloromethane) to give product as an oil (0.29 g, 82%); MS for C36H42N4O4 m/z 595 (M+H)+.

Workup

  1. washwashed with water and brine
  2. dry with materialdried (MgSO4)
  3. customevaporated
  4. customThe residue was purified by PTLC (5% methanol/dichloromethane)

Sources & evidence

ORD record
ord-cb1c7166a0c34944a03dc395b1d5c463
Source dataset
uspto-grants-2014_04
Patent number
US08691836B2

Reaction notes

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