Ethyl Bromide → HCID 59146149, compound

HRID 1512821Notes

Reaction equation

HRID 1512821 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].Br[CH2:34][CH3:35].[C:36](OCC)(=O)[CH3:37]>CS(C)=O>[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]([CH2:36][CH3:37])[CH:25]=[C:24]4[CH2:28][CH2:29][C:30]([O:32][CH2:34][CH3:35])=[O:31])[N:15]=2)[CH:7]=[CH:8][C:9]=1[O:10][CH:11]([CH3:12])[CH3:13]

Participants

6

Reactant 4

HCID 6332Ethyl BromideHCID 8857Ethyl AcetateHCID 14797Potassium HydroxideHCID 44547315HCID 44547315, compound

Product 1

HCID 59146149HCID 59146149, compound

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

Potassium hydroxide (62 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 bromoethane (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 anhydrous sodium sulfate. After concentration, the residue was purified via column chromatography to afford ethyl 3-[7-(5-{3-chloro-4-[(1-methylethyl)oxy]phenyl}-1,2,4-oxadiazol-3-yl)-1-ethyl-1H-indol-3-yl]propanoate (D120) (79 mg). δH (CDCl3, 400 MHz): 1.14 (3H, t), 1.25 (3H, t), 1.45 (6H, d), 2.71 (2H, t), 3.12 (2H, t), 4.15 (2H, q), 4.20 (2H, q), 4.72 (1H, m), 6.97 (1H, s), 7.07 (1H, d), 7.20 (1H, t), 7.55 (1H, dd), 7.76 (1H, dd), 8.08 (1H, dd), 8.26 (1H, d); MS (ES): C26H28ClN3O4 requires 481; found 482.2 (M+H+).

Workup

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

Sources & evidence

ORD record
ord-4e3a6c240e8b40eabbc1b7902cfbfbb4
Source dataset
uspto-grants-2012_07
Patent number
US08217028B2

Reaction notes

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