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

HRID 1751071Notes

Reaction equation

HRID 1751071 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:31]=[CH:30][CH:29]=[CH:28][C:20]=1[C:21]([O:23][C:24]([CH3:27])([CH3:26])[CH3:25])=[O:22].[I-].[Na+].C(=O)([O-])[O-].[K+].[K+].Cl[CH2:41][CH2:42][CH2:43][N:44]1[C:52]2[C:47](=[CH:48][CH:49]=[CH:50][CH:51]=2)[C:46]([CH3:54])([CH3:53])[C:45]1=[O:55]>CC(=O)CC>[CH3:54][C:46]1([CH3:53])[C:47]2[C:52](=[CH:51][CH:50]=[CH:49][CH:48]=2)[N:44]([CH2:43][CH2:42][CH2:41][N:9]2[CH2:8][CH2:7][C:6]3([N:5]([C:12]4[CH:13]=[CH:14][CH:15]=[CH:16][CH:17]=4)[CH2:4][N:3]([CH2:18][C:19]4[CH:31]=[CH:30][CH:29]=[CH:28][C:20]=4[C:21]([O:23][C:24]([CH3:27])([CH3:25])[CH3:26])=[O:22])[C:2]3=[O:1])[CH2:11][CH2:10]2)[C:45]1=[O:55]

Participants

6

Reactant 4

HCID 5238Sodium IodideHCID 11430Potassium CarbonateHCID 580466771-(3-Chloropropyl)-3,3-dimethylindolin-2-oneHCID 66652177Tert-butyl 2-((4-oxo-1-phenyl-1,3,8-triazaspiro[4.5]decan-3-yl)methyl)benzoate

Product 1

HCID 58046809Tert-butyl 2-((8-(3-(3,3-dimethyl-2-oxoindolin-1-yl)propyl)-4-oxo-1-phenyl-1,3,8-triazaspiro[4.5]decan-3-yl)methyl)benzoateYield 69%

Reagents, catalysts & solvents 1

HCID 6569Methyl Ethyl KetoneSolvent

Conditions

Temperature
78 °C

Procedure

To a solution of tert-butyl 2-((4-oxo-1-phenyl-1,3,8-triazaspiro[4.5]decan-3-yl)methyl)benzoate (0.175 g, 0.42 mmol), sodium iodide (0.019 g, 0.13 mmol) and potassium carbonate (0.087 g, 0.63 mmol) in 2-butanone (5 mL), was added 1-(3-chloropropyl)-3,3-dimethylindolin-2-one (0.098 g, 0.42 mmol). After stirring at 78° C. for 18 hours, the reaction mixture was filtered and isolated by preparatory TLC (10% methanol/dichloromethane) to obtain the title compound (0.18 g, 69%); 1H NMR (DMSO-d6): δ 1.26 (s, 6H), 1.57 (s, 9H), 1.67 (d, 2H, J=12.4 Hz), 1.75-1.76 (m, 2H), 2.32-2.33 (m, 2H), 2.50-2.72 (m, 6H), 3.74 (t, 2H, J=6.4 Hz), 4.61 (s, 2H), 4.84 (s, 2H), 6.76 (t, 1H, J=7.2 Hz), 6.84 (d, 2H, J=8 Hz), 7.02 (t, 1H, J=6.8 Hz), 7.13 (d, 1H, J=7.6 Hz), 7.23-7.31 (m, 4H), 7.34 (d, 1H, J=6.8 Hz), 7.41 (t, 1H, J=7.2 Hz), 7.57 (t, 1H, J=8.8 Hz), 7.82 (d, 1H, J=7.2 Hz); MS for C38H46N4O4 m/z 623.28 (M+H)+.

Workup

  1. filtrationthe reaction mixture was filtered
  2. customisolated by preparatory TLC (10% methanol/dichloromethane)

Sources & evidence

ORD record
ord-b02048b5523d4b389c381d48d4c24692
Source dataset
uspto-grants-2015_10
Patent number
US09156840B2

Reaction notes

Loading…