3-(1-bromo-imidazo[1,5-a]pyridin-6-yl)-2,2-dimethyl-3-phenylpropanoic acid

Base Information

• Chemical Name: 3-(1-bromo-imidazo[1,5-a]pyridin-6-yl)-2,2-dimethyl-3-phenylpropanoic acid
• CAS No.: 1025482-61-4
• Molecular Formula: C₁₈H₁₇BrN₂O₂
• Molecular Weight: 373.249
• Mol file: 1025482-61-4.mol

Synonyms:3-(1-bromo-imidazo[1,5-a]pyridin-6-yl)-2,2-dimethyl-3-phenylpropanoic acid

Chemical Property of 3-(1-bromo-imidazo[1,5-a]pyridin-6-yl)-2,2-dimethyl-3-phenylpropanoic acid

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 3-(1-bromo-imidazo[1,5-a]pyridin-6-yl)-2,2-dimethyl-3-phenylpropanoic acid

There total 8 articles about 3-(1-bromo-imidazo[1,5-a]pyridin-6-yl)-2,2-dimethyl-3-phenylpropanoic acid 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: 100.0%

methyl 3-(1-bromo-imidazo[1,5-a]pyridin-6-yl)-2,2-dimethyl-3-phenylpropanoate (1025482-57-8) → 3-(1-bromo-imidazo[1,5-a]pyridin-6-yl)-2,2-dimethyl-3-phenylpropanoic acid (1025482-61-4)

Guidance literature:

With lithium hydroxide; In 1,4-dioxane; water;

DOI:10.1016/j.bmcl.2013.08.049

Reference yield:

6-chloronicotinylaldehyde (23100-12-1) → 3-(1-bromo-imidazo[1,5-a]pyridin-6-yl)-2,2-dimethyl-3-phenylpropanoic acid (1025482-61-4)

Guidance literature:

Multi-step reaction with 9 steps

1: phenylmagnesium bromide / tetrahydrofuran

2: N-ethyl-N,N-diisopropylamine; dmap / dichloromethane

3: titanium tetrachloride / dichloromethane

4: dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH₂Cl₂; zinc / N,N-dimethyl acetamide / 2 h / 120 °C

5: hydrogen; palladium on activated charcoal; hydrogenchloride / methanol / 2.5 h

6: 90 °C

7: trichlorophosphate / toluene / 115 °C

8: N-Bromosuccinimide / acetonitrile / -10 - 20 °C

9: lithium hydroxide / water; 1,4-dioxane

With hydrogenchloride; dmap; N-Bromosuccinimide; dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH₂Cl₂; palladium on activated charcoal; hydrogen; titanium tetrachloride; N-ethyl-N,N-diisopropylamine; phenylmagnesium bromide; lithium hydroxide; zinc; trichlorophosphate; In tetrahydrofuran; 1,4-dioxane; methanol; dichloromethane; N,N-dimethyl acetamide; water; toluene; acetonitrile;

DOI:10.1016/j.bmcl.2013.08.049

Reference yield:

6-chloro-α-phenyl-3-pyridinemethanol (80100-47-6) → 3-(1-bromo-imidazo[1,5-a]pyridin-6-yl)-2,2-dimethyl-3-phenylpropanoic acid (1025482-61-4)

Guidance literature:

Multi-step reaction with 8 steps

1: N-ethyl-N,N-diisopropylamine; dmap / dichloromethane

2: titanium tetrachloride / dichloromethane

3: dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH₂Cl₂; zinc / N,N-dimethyl acetamide / 2 h / 120 °C

4: hydrogen; palladium on activated charcoal; hydrogenchloride / methanol / 2.5 h

5: 90 °C

6: trichlorophosphate / toluene / 115 °C

7: N-Bromosuccinimide / acetonitrile / -10 - 20 °C

8: lithium hydroxide / water; 1,4-dioxane

With hydrogenchloride; dmap; N-Bromosuccinimide; dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH₂Cl₂; palladium on activated charcoal; hydrogen; titanium tetrachloride; N-ethyl-N,N-diisopropylamine; lithium hydroxide; zinc; trichlorophosphate; In 1,4-dioxane; methanol; dichloromethane; N,N-dimethyl acetamide; water; toluene; acetonitrile;

DOI:10.1016/j.bmcl.2013.08.049

upstream raw materials:

6-chloronicotinylaldehyde

6-chloro-α-phenyl-3-pyridinemethanol

acetic acid (6-chloro-pyridin-3-yl)-phenyl-methyl ester

3-(6-chloro-pyridin-3-yl)-2,2-dimethyl-3-phenyl-propionic acid methyl ester

Downstream raw materials:

3-(1-(3-cyanophenyl)-imidazo[1,5-a]pyridin-6-yl)-2,2-dimethyl-3-phenyl-N-(thiazol-2-yl)propanamide

C₂₇H₂₂N₆OS

C₂₈H₂₃N₅OS

C₂₇H₂₂N₆OS