Potassium Carbonate → HCID 86677483, compound

HRID 1621126Notes

Reaction equation

HRID 1621126 reaction equation
[CH3:1][C:2]1[NH:6][N:5]=[C:4]([C:7]2[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=2)[N:3]=1.C(=O)([O-])[O-].[K+].[K+].Br[CH2:20][CH2:21][NH:22][C:23](=[O:29])[O:24][C:25]([CH3:28])([CH3:27])[CH3:26]>CN(C=O)C>[CH3:1][C:2]1[N:6]([CH2:20][CH2:21][NH:22][C:23](=[O:29])[O:24][C:25]([CH3:28])([CH3:27])[CH3:26])[N:5]=[C:4]([C:7]2[CH:8]=[CH:9][CH:10]=[CH:11][CH:12]=2)[N:3]=1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 5943815-methyl-3-phenyl-1H-1,2,4-triazoleHCID 4103526tert-Butyl N-(2-bromoethyl)carbamate

Product 1

HCID 86677483HCID 86677483, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

5-Methyl-3-phenyl-1H-1,2,4-triazole (120 mg, 754 μmol) was dissolved in DMF (2.4 mL) and potassium carbonate (208 mg, 1.51 mmol) was added. After 20 min tert-butyl 2-bromoethylcarbamate (186 mg, 829 μmol) was added at 0-5° C. and the reaction mixture was stirred at RT for 25 h. The reaction mixture was extracted with ethyl acetate (30 mL) and washed with water (3×50 mL). The aqueous layers were back-extracted with ethyl acetate (20 mL) and the combined organic layer was dried over MgSO4 and concentrated in vacuo. The product was obtained after purification by flash chromatography (using silica gel and an ethyl acetate/heptane gradient) as white solid (237 mg, 784 μmol, 83.2%).

Workup

  1. extractionThe reaction mixture was extracted with ethyl acetate (30 mL)
  2. washwashed with water (3×50 mL)
  3. extractionThe aqueous layers were back-extracted with ethyl acetate (20 mL)
  4. dry with materialthe combined organic layer was dried over MgSO4
  5. concentrationconcentrated in vacuo
  6. customThe product was obtained
  7. customafter purification by flash chromatography (

Sources & evidence

ORD record
ord-eb6745774e6842659b87fa0756d1ffb2
Source dataset
uspto-grants-2014_07
Patent number
US08772510B2

Reaction notes

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