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

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)

1. temperatureto cool
2. custompartitioned between diethyl ether (50 mL) and water (30 mL)
3. customThe organic layer was separated
4. washwashed with water (3×)
5. dry with materialdried over magnesium sulfate
6. filtrationfiltered
7. concentrationconcentrated under reduced pressure
8. dissolutionThe resulting residue was dissolved in ethyl acetate
9. concentrationethanol (2:1 mixture) and concentrated onto silica gel
10. custompurified by flash column chromatography

ORD-Eintrag

ord-2bb98687a5ec438ea5f779a24e8a0a21

Quelldatensatz

uspto-grants-2014_09

DOI

10.6084/m9.figshare.5104873.v1

Patentnummer

US08822521B2