Isobutyl iodide → HCID 59146116, compound

HRID 1512823Notes

Reaction equation

HRID 1512823 reaction equation
[OH-].[K+].[Cl:3][C:4]1[CH:5]=[C:6]([C:14]2[O:18][N:17]=[C:16]([C:19]3[CH:20]=[CH:21][CH:22]=[C:23]4[C:27]=3[NH:26][CH:25]=[C:24]4[CH2:28][CH2:29][C:30]([OH:32])=[O:31])[N:15]=2)[CH:7]=[CH:8][C:9]=1[O:10][CH:11]([CH3:13])[CH3:12].I[CH2:34][CH:35]([CH3:37])[CH3:36]>CS(C)=O.C(OCC)(=O)C>[Cl:3][C:4]1[CH:5]=[C:6]([C:14]2[O:18][N:17]=[C:16]([C:19]3[CH:20]=[CH:21][CH:22]=[C:23]4[C:27]=3[N:26]([CH2:34][CH:35]([CH3:37])[CH3:36])[CH:25]=[C:24]4[CH2:28][CH2:29][C:30]([O:32][CH2:5][CH:6]([CH3:14])[CH3:7])=[O:31])[N:15]=2)[CH:7]=[CH:8][C:9]=1[O:10][CH:11]([CH3:12])[CH3:13]

Participants

6

Reactant 3

HCID 10556Isobutyl iodideHCID 14797Potassium HydroxideHCID 44547315HCID 44547315, compound

Product 1

HCID 59146116HCID 59146116, compound

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolventHCID 8857Ethyl AcetateSolvent

Procedure

Potassium hydroxide (64 mg) was added to a solution of 3-[7-(5-{3-chloro-4-[(1-methylethyl)oxy]phenyl}-1,2,4-oxadiazol-3-yl)-1H-indol-3-yl]propanoic acid (E1) (100 mg) and 1-iodo-2-methylpropane (0.2 mL) in dimethyl sulfoxide (DMSO) (1 mL). The reaction mixture was stirred at room temperature for 3 hours. The reaction mixture was diluted with ethyl acetate. The organic solution was washed with water. The organic solution was dried over sodium sulfate. After concentration, the residue was purified via column chromatography to afford 2-methylpropyl 3-[7-(5-{3-chloro-4-[(1-methylethyl)oxy]phenyl}-1,2,4-oxadiazol-3-yl)-1-(2-methylpropyl)-1H-indol-3-yl]propanoate (D124) (77 mg). MS (ES): C30H36ClN3O4 requires 537; found 538.3 (M+H+).

Workup

  1. washThe organic solution was washed with water
  2. dry with materialThe organic solution was dried over sodium sulfate
  3. concentrationAfter concentration
  4. customthe residue was purified via column chromatography

Sources & evidence

ORD record
ord-cd45560d7f3841a285513454f1ba1272
Source dataset
uspto-grants-2012_07
Patent number
US08217028B2

Reaction notes

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