反応 #157432

反応方程式

methyl N-[[2-chloro-5-(1H-1,2,3-triazol-5-yl)phenyl]methyl]carbamate

4-methylbenzyl bromide

potassium carbonate

→

methyl N-[[2-chloro-5-[2-[(4-methylphenyl)methyl]-2H-1,2,3-triazol-4-yl]phenyl]methyl]carbamate

溶媒

N,N-dimethylformamide

反応条件

後処理

1. 1
   温度to cool
2. 2
   その他partitioned between diethyl ether (50 mL) and water (30 mL)
3. 3
   その他The organic layer was separated
4. 4
   洗浄washed with water (3×)
5. 5
   乾燥dried over magnesium sulfate
6. 6
   ろ過filtered
7. 7
   濃縮concentrated under reduced pressure
8. 8
   workup.DISSOLUTIONThe resulting residue was dissolved in ethyl acetate
9. 9
   濃縮ethanol (2:1 mixture) and concentrated onto silica gel
10. 10
    その他purified by flash column chromatography

実験手順

A mixture of methyl N-[[2-chloro-5-(1H-1,2,3-triazol-5-yl)phenyl]methyl]carbamate (i.e. the product of Step E, Example 9) (0.24, 0.9 mmol), 4-methylbenzyl bromide (0.17 g, 1.1 mmol) and potassium carbonate (0.25 g, 1.8 mmol) in N,N-dimethylformamide (4.5 mL) was heated at 100° C. for 24 h. The reaction mixture was allowed to cool and then partitioned between diethyl ether (50 mL) and water (30 mL). The organic layer was separated, washed with water (3×), dried over magnesium sulfate, filtered and concentrated under reduced pressure. The resulting residue was dissolved in ethyl acetate and ethanol (2:1 mixture) and concentrated onto silica gel, and then purified by flash column chromatography using 5 g of silica gel (0 to 50% gradient of ethyl acetate in hexanes as eluant) to provide methyl N-[[2-chloro-5-[2-[(4-methylphenyl)methyl]-2H-1,2,3-triazol-4-yl]phenyl]methyl]carbamate, a compound of the present invention, as a colorless oil (0.11 g)

出典