Imidazole → 4-Chloro-1-(cyclopropylmethyl)-5-[4-(iodomethyl)cyclohex-1-en-1-yl]-1H-benzotriazole

To a tetrahydrofuran solution (2 mL) of triphenylphosphine (94 mg, 0.36 mmol, 1.1 equiv) was added imidazole (0.11 g, 1.6 mmol, 5 equiv) and iodine (86 mg, 0.34 mmol, 1.05 equiv). After stirring for 10 minutes, a tetrahydrofuran solution (1.5 mL) of {4-[4-chloro-1-(cyclopropylmethyl)-1H-benzotriazol-5-yl]cyclohex-3-en-1-yl}methanol (Example 2, 0.10 g, 0.32 mmol) was added and the mixture was stirred for 1 hour. In a separate flask, a tetrahydrofuran solution (2 mL) was prepared containing triphenylphosphine (94 mg, 0.36 mmol, 1.1 equiv), imidazole (0.11 g, 1.6 mmol, 5 equiv) and iodine (86 mg, 0.34 mmol, 1.05 equiv), which was added to the reaction mixture after stirring for 10 minutes. After stirring for an additional 1 hour, an additional tetrahydrofuran solution (2 mL) containing triphenylphosphine (94 mg, 0.36 mmol, 1.1 equiv), imidazole (0.11 g, 1.6 mmol, 5 equiv) and iodine (86 mg, 0.34 mmol, 1.05 equiv) was added to the reaction mixture. After stirring for an additional 30 minutes, the mixture was purified by silica gel gradient chromatography (100:0 to 0:100; hexanes:ethly acetate), providing the titled compound as a light yellow oil.

1. stirringthe mixture was stirred for 1 hour
2. additionwas added to the reaction mixture
3. stirringafter stirring for 10 minutes
4. stirringAfter stirring for an additional 1 hour
5. additionwas added to the reaction mixture
6. stirringAfter stirring for an additional 30 minutes
7. customthe mixture was purified by silica gel gradient chromatography (100:0 to 0:100; hexanes:ethly acetate)

ORD record

ord-d7995481331540a08c9f82812cacf781

Source dataset

uspto-grants-2014_07

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08785482B2