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

HRID 2362987Notes

Reaction equation

HRID 2362987 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]2[C:12]3([CH2:17][CH2:16][NH:15][CH2:14][CH2:13]3)[C:11](=[O:18])[N:10]([CH2:19][C:20]3[CH:21]=[C:22]([CH:30]=[CH:31][CH:32]=3)[C:23]([O:25][C:26]([CH3:29])([CH3:28])[CH3:27])=[O:24])[CH2:9]2)=[CH:4][CH:3]=1.[I-].[Na+].C(=O)([O-])[O-].[K+].[K+].Cl[CH2:42][CH2:43][CH2:44][N:45]1[C:53]2[C:48](=[CH:49][CH:50]=[CH:51][CH:52]=2)[C:47]([CH3:55])([CH3:54])[C:46]1=[O:56]>CC(=O)CC>[CH3:55][C:47]1([CH3:54])[C:48]2[C:53](=[CH:52][CH:51]=[CH:50][CH:49]=2)[N:45]([CH2:44][CH2:43][CH2:42][N:15]2[CH2:14][CH2:13][C:12]3([N:8]([C:5]4[CH:4]=[CH:3][C:2]([F:1])=[CH:7][CH:6]=4)[CH2:9][N:10]([CH2:19][C:20]4[CH:21]=[C:22]([CH:30]=[CH:31][CH:32]=4)[C:23]([O:25][C:26]([CH3:27])([CH3:28])[CH3:29])=[O:24])[C:11]3=[O:18])[CH2:17][CH2:16]2)[C:46]1=[O:56]

Participants

6

Reactant 4

HCID 5238Sodium IodideHCID 11430Potassium CarbonateHCID 580466771-(3-Chloropropyl)-3,3-dimethylindolin-2-oneHCID 66652535Tert-butyl 3-((1-(4-fluorophenyl)-4-oxo-1,3,8-triazaspiro[4.5]decan-3-yl)methyl)benzoate

Product 1

HCID 58046669Tert-butyl 3-((8-(3-(3,3-dimethyl-2-oxoindolin-1-yl)propyl)-1-(4-fluorophenyl)-4-oxo-1,3,8-triazaspiro[4.5]decan-3-yl)methyl)benzoateYield 78%

Reagents, catalysts & solvents 1

HCID 6569Methyl Ethyl KetoneSolvent

Conditions

Temperature
78 °C

Procedure

To a solution of tert-butyl 3-((1-(4-fluorophenyl)-4-oxo-1,3,8-triazaspiro[4.5]decan-3-yl)methyl)benzoate (1.2 g, 2.84 mmol), sodium iodide (0.015 g, 0.1 mmol) and potassium carbonate (0.07 g, 0.51 mmol) in 2-butanone (3 mL), was added 1-(3-chloropropyl)-3,3-dimethylindolin-2-one (0.081 g, 0.34 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 (0.17 g, 78%); 1H NMR (DMSO-d6): δ 1.26 (s, 6H), 1.51 (s, 9H), 1.63 (d, 2H, J=12.4 Hz), 1.75-1.76 (m, 2H), 2.29-2.32 (m, 4H), 2.66-2.67 (m, 4H), 3.72 (t, 2H, J=6.8 Hz), 4.57 (d, 2H, J=14.8 Hz), 6.91 (s, 2H), 7.02 (t, 1H, J=7.2 Hz), 7.07-7.09 (m, 3H), 7.22 (t, 1H, J=7.2 Hz), 7.34 (d, 1H, J=7.2 Hz), 7.47-7.54 (m, 2H), 7.78 (s, 1H), 7.82 (d, 1H, J=6.8 Hz).

Workup

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

Sources & evidence

ORD record
ord-bce17f953c2247b88f0292a38a607366
Source dataset
uspto-grants-2014_04
Patent number
US08691836B2

Reaction notes

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