1,1'-Carbonyldiimidazole → HCID 70102281, compound

HRID 2301329Notes

Reaction equation

HRID 2301329 reaction equation
C1N=CN([C:6]([N:8]2C=N[CH:10]=[CH:9]2)=[O:7])C=1.[CH2:13]([O:15][C:16]([C:18]1[C:26]2[C:21](=[CH:22][C:23]([Br:31])=[C:24]([CH2:27]C(O)=O)[CH:25]=2)[NH:20][C:19]=1[CH3:32])=[O:17])[CH3:14].CO[C:35]1[CH:36]=[C:37]([CH2:41]CN)[CH:38]=[CH:39][CH:40]=1>C1COCC1>[CH2:13]([O:15][C:16]([C:18]1[C:26]2[C:21](=[CH:22][C:23]([Br:31])=[C:24]([CH2:27][C:6](=[O:7])[NH:8][CH2:9][CH2:10][C:35]3[CH:40]=[CH:39][CH:38]=[C:37]([CH3:41])[CH:36]=3)[CH:25]=2)[NH:20][C:19]=1[CH3:32])=[O:17])[CH3:14]

Participants

5

Reactant 3

HCID 682631,1'-CarbonyldiimidazoleHCID 748663-MethoxyphenethylamineHCID 18344915HCID 18344915, compound

Product 1

HCID 70102281HCID 70102281, compoundYield 84%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a solution of CDI (0.93 g, 5.7 mmol) in THF (50 mL) is added a solution of 6-bromo-5-carboxymethyl-2-methyl-1H-indole-3-carboxylic acid ethyl ester in THF (50 mL). The mixture is stirred at room temperature for 45 minutes, then refluxed for 1 hour. After cooling the reaction mixture to room temperature, 2-(3-methoxyphenyl)ethylamine is added and resulting reaction mixture is stirred at room temperature overnight. The reaction mixture is concentrated in vacuo, ethyl acetate (150 mL) is added, then washed with 1N HCl (50 mL), 1N NaOH (50 mL), and brine (50 mL). The organic layer is dried (Na2SO4) and concentrated in vacuo to give the desired product (2.15 g, 84%). MS: 473, 475 (M+1)+.

Workup

  1. temperaturerefluxed for 1 hour
  2. temperatureAfter cooling the reaction mixture to room temperature
  3. customresulting
  4. customreaction mixture
  5. stirringis stirred at room temperature overnight
  6. concentrationThe reaction mixture is concentrated in vacuo, ethyl acetate (150 mL)
  7. additionis added
  8. washwashed with 1N HCl (50 mL), 1N NaOH (50 mL), and brine (50 mL)
  9. dry with materialThe organic layer is dried (Na2SO4)
  10. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-fee0d68d0ee3414c9e9eab3bd2a4bd50
Source dataset
uspto-grants-2002_12
Patent number
US06500837B2

Reaction notes

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