Butyl iodide → HCID 59146037, compound

HRID 1512822Notes

Reaction equation

HRID 1512822 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][CH2:35][CH2:36][CH3:37]>CS(C)=O.C(OCC)(=O)C>[CH2:34]([N:26]1[C:27]2[C:23](=[CH:22][CH:21]=[CH:20][C:19]=2[C:16]2[N:15]=[C:14]([C:6]3[CH:7]=[CH:8][C:9]([O:10][CH:11]([CH3:12])[CH3:13])=[C:4]([Cl:3])[CH:5]=3)[O:18][N:17]=2)[C:24]([CH2:28][CH2:29][C:30]([O:32][CH2:5][CH2:4][CH2:9][CH3:8])=[O:31])=[CH:25]1)[CH2:35][CH2:36][CH3:37]

Participants

6

Reactant 3

HCID 10962Butyl iodideHCID 14797Potassium HydroxideHCID 44547315HCID 44547315, compound

Product 1

HCID 59146037HCID 59146037, compound

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolventHCID 8857Ethyl AcetateSolvent

Procedure

Potassium hydroxide (65 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-iodobutane (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 butyl 3-[1-butyl-7-(5-{3-chloro-4-[(1-methylethyl)oxy]phenyl}-1,2,4-oxadiazol-3-yl)-1H-indol-3-yl]propanoate (D123) (61 mg). δH (CDCl3, 400 MHz): 0.73 (3H, t), 0.92 (3H, t), 1.03 (2H, m), 1.34 (2H, m), 1.45 (8H, m), 1.59 (2H, m), 2.71 (2H, t), 3.12 (2H, t), 4.08 (2H, t), 4.16 (2H, t), 4.72 (1H, m), 6.94 (1H, s), 7.07 (1H, d), 7.19 (1H, t), 7.53 (1H, dd), 7.76 (1H, dd), 8.08 (1H, dd), 8.25 (1H, d); 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-f41319583eec41579050f35191a85ee4
Source dataset
uspto-grants-2012_07
Patent number
US08217028B2

Reaction notes

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