Tetrahydrofuran → [2-Fluoro-4-(4-[1,2,3]triazol-1-yl-butyl)-phenyl]-carbamic acid tert-butyl ester

To a solution of 1-but-3-enyl-1H-[1,2,3]triazole (0.85 g, 6.9 mmol) in THF (15 ml) 9-borabicyclo[3.3.1]nonane (0.5 M in THF, 30.3 ml, 15.2 mmol) was added dropwise at 0° C. and stirring continued for 2 h. This mixture was then added to a solution of (4-bromo-2-fluoro-phenyl)-carbamic acid tert-butyl ester (2 g, 6.89 mmol), Pd(dppf)Cl2 (0.56 g, 0.69 mmol) and aqueous cesium carbonate (6.89 ml, 3M) in DMF (30 ml) and stirred for 3 h at 70° C. Water (100 ml) was added and the mixture extracted with ethyl acetate (3×100 ml). The combined organic layers were washed with water and brine, dried over sodium sulfate and concentrated. The crude product was purified on silica gel (ethyl acetate) to yield [2-Fluoro-4-(4-[1,2,3]triazol-1-yl-butyl)-phenyl]-carbamic acid tert-butyl ester as light yellow solid. Yield 1.93 g (84%)

1. stirringstirred for 3 h at 70° C
2. extractionthe mixture extracted with ethyl acetate (3×100 ml)
3. washThe combined organic layers were washed with water and brine
4. dry with materialdried over sodium sulfate
5. concentrationconcentrated
6. customThe crude product was purified on silica gel (ethyl acetate)

ORD record

ord-01ef786061ec438693154980bc49804b

Source dataset

uspto-grants-2008_03

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07342030B2