2-{(1-cyclopropylmethyl-piperidin-4-ylidene)-[4-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-phenyl]-methyl}-5-fluoro-6-trifluoromethyl-1H-benzoimidazole

Base Information

Chemical Name:2-{(1-cyclopropylmethyl-piperidin-4-ylidene)-[4-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-phenyl]-methyl}-5-fluoro-6-trifluoromethyl-1H-benzoimidazole
CAS No.:911469-22-2
Molecular Formula:C₃₀H₃₄BF₄N₃O₂
Molecular Weight:555.423
Hs Code.:

2-{(1-cyclopropylmethyl-piperidin-4-ylidene)-[4-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-phenyl]-methyl}-5-fluoro-6-trifluoromethyl-1<i>H</i>-benzoimidazole

Synonyms:2-{(1-cyclopropylmethyl-piperidin-4-ylidene)-[4-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-phenyl]-methyl}-5-fluoro-6-trifluoromethyl-1H-benzoimidazole

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Chemical Property of 2-{(1-cyclopropylmethyl-piperidin-4-ylidene)-[4-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-phenyl]-methyl}-5-fluoro-6-trifluoromethyl-1H-benzoimidazole

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Technology Process of 2-{(1-cyclopropylmethyl-piperidin-4-ylidene)-[4-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-phenyl]-methyl}-5-fluoro-6-trifluoromethyl-1H-benzoimidazole

There total 7 articles about 2-{(1-cyclopropylmethyl-piperidin-4-ylidene)-[4-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-phenyl]-methyl}-5-fluoro-6-trifluoromethyl-1H-benzoimidazole which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 47.0%

: 903899-11-6
2-[(4-bromo-phenyl)-(1-cyclopropylmethyl-piperidin-4-ylidene)-methyl]-5-fluoro-6-trifluoromethyl-1H-benzoimidazole

: 73183-34-3
bis(pinacol)diborane

: 911469-22-2
2-{(1-cyclopropylmethyl-piperidin-4-ylidene)-[4-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-phenyl]-methyl}-5-fluoro-6-trifluoromethyl-1H-benzoimidazole

Guidance literature:: With palladium bis[bis(diphenylphosphino)ferrocene] dichloride; potassium acetate; In dimethyl sulfoxide; at 100 ℃;
DOI:10.1016/j.bmcl.2006.04.062

Reference yield:

: 846049-52-3
4-[1-(4-bromo-phenyl)-2-oxo-ethylidene]-piperidine-1-carboxylic acid tert-butyl ester

: 911469-22-2
2-{(1-cyclopropylmethyl-piperidin-4-ylidene)-[4-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-phenyl]-methyl}-5-fluoro-6-trifluoromethyl-1H-benzoimidazole

Guidance literature:: Multi-step reaction with 4 steps

1: aq. NaHSO₃ / ethanol

2: TFA / CH₂Cl₂

3: NaBH(OAc)3 / CH₂Cl₂

4: 47 percent / KOAc; PdCl₂(dppf)2 / dimethylsulfoxide / 100 °C

With palladium bis[bis(diphenylphosphino)ferrocene] dichloride; potassium acetate; sodium tris(acetoxy)borohydride; sodium hydrogensulfite; trifluoroacetic acid; In ethanol; dichloromethane; dimethyl sulfoxide;
DOI:10.1016/j.bmcl.2006.04.062

Reference yield:

: 846049-50-1
4-[(4-bromo-phenyl)-cyano-methylene]-piperidine-1-carboxylic acid tert-butyl ester

: 911469-22-2
2-{(1-cyclopropylmethyl-piperidin-4-ylidene)-[4-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-phenyl]-methyl}-5-fluoro-6-trifluoromethyl-1H-benzoimidazole

Guidance literature:: Multi-step reaction with 5 steps

1: 38 percent / DIBAL / CH₂Cl₂ / -78 °C

2: aq. NaHSO₃ / ethanol

3: TFA / CH₂Cl₂

4: NaBH(OAc)3 / CH₂Cl₂

5: 47 percent / KOAc; PdCl₂(dppf)2 / dimethylsulfoxide / 100 °C

With palladium bis[bis(diphenylphosphino)ferrocene] dichloride; potassium acetate; sodium tris(acetoxy)borohydride; diisobutylaluminium hydride; sodium hydrogensulfite; trifluoroacetic acid; In ethanol; dichloromethane; dimethyl sulfoxide;
DOI:10.1016/j.bmcl.2006.04.062