(S)-2-[3-(2-Benzyloxy-1-methylethyl)-2-(3,5-dimethyl-phenyl)-1H-pyrrolo[2,3-b]pyridin-5-yl]-2-methylpropanoic acid

Base Information

• Chemical Name: (S)-2-[3-(2-Benzyloxy-1-methylethyl)-2-(3,5-dimethyl-phenyl)-1H-pyrrolo[2,3-b]pyridin-5-yl]-2-methylpropanoic acid
• CAS No.: 246224-05-5
• Molecular Formula: C₂₉H₃₂N₂O₃
• Molecular Weight: 456.585

Synonyms:(S)-2-[3-(2-Benzyloxy-1-methylethyl)-2-(3,5-dimethyl-phenyl)-1H-pyrrolo[2,3-b]pyridin-5-yl]-2-methylpropanoic acid

Chemical Property of (S)-2-[3-(2-Benzyloxy-1-methylethyl)-2-(3,5-dimethyl-phenyl)-1H-pyrrolo[2,3-b]pyridin-5-yl]-2-methylpropanoic acid

Chemical Property:

Purity/Quality:

98% ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (S)-2-[3-(2-Benzyloxy-1-methylethyl)-2-(3,5-dimethyl-phenyl)-1H-pyrrolo[2,3-b]pyridin-5-yl]-2-methylpropanoic acid

There total 9 articles about (S)-2-[3-(2-Benzyloxy-1-methylethyl)-2-(3,5-dimethyl-phenyl)-1H-pyrrolo[2,3-b]pyridin-5-yl]-2-methylpropanoic 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:

methyl (S)-2-[3-(2-benzyloxy-1-methylethyl)-2-(3,5-dimethyl-phenyl)-1H-pyrrolo[2,3-b]pyridin-5-yl]-2-methylpropanoate (246219-76-1) → (S)-2-[3-(2-Benzyloxy-1-methylethyl)-2-(3,5-dimethyl-phenyl)-1H-pyrrolo[2,3-b]pyridin-5-yl]-2-methylpropanoic acid (246224-05-5)

Guidance literature:

With potassium hydroxide; In methanol; at 65 ℃;

DOI:10.1016/S0040-4039(01)01322-3

Reference yield:

ethyl 2-methyl-2-(pyridin-3-yl)propionate (120690-70-2) → (S)-2-[3-(2-Benzyloxy-1-methylethyl)-2-(3,5-dimethyl-phenyl)-1H-pyrrolo[2,3-b]pyridin-5-yl]-2-methylpropanoic acid (246224-05-5)

Guidance literature:

Multi-step reaction with 9 steps

1: 92 percent / m-CPBA; NaHCO₃ / CHCl₃; H₂O / 12 h / 20 °C

2: 84 percent / 1,2-dichloro-ethane / 72 h / 82 °C

3: 88 percent / HCl / 8 h / 100 °C

4: 100 percent / H₂SO₄ / 15 h / 65 °C

5: 62 percent / I₂ / AgCO₂CF₃ / methanol / 15 h / 20 °C

6: 95 percent / LiCl; Na₂CO₃ / Pd(dppf)Cl₂*CH₂Cl₂ / dimethylformamide / 15 h / 100 °C

7: 84 percent / ICl; AgBF₄ / methanol; tetrahydrofuran / 1 h / 20 °C

8: 100 percent / Na₂CO₃ / Pd(dppf)Cl₂*CH₂Cl₂ / ethanol; toluene / 15 h / 85 °C

9: KOH / methanol / 65 °C

With potassium hydroxide; silver tetrafluoroborate; sulfuric acid; iodine; Iodine monochloride; sodium hydrogencarbonate; sodium carbonate; 3-chloro-benzenecarboperoxoic acid; lithium chloride; hydrogenchloride; dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH₂Cl₂; silver trifluoroacetate; In tetrahydrofuran; methanol; ethanol; chloroform; water; 1,2-dichloro-ethane; N,N-dimethyl-formamide; toluene; 8: Suzuki-Miayura cross-coupling;

DOI:10.1016/S0040-4039(01)01322-3

Reference yield:

2-(6-amino-pyridin-3-yl)-2-methyl-propionic acid methyl ester (246219-79-4) → (S)-2-[3-(2-Benzyloxy-1-methylethyl)-2-(3,5-dimethyl-phenyl)-1H-pyrrolo[2,3-b]pyridin-5-yl]-2-methylpropanoic acid (246224-05-5)

Guidance literature:

Multi-step reaction with 5 steps

1: 62 percent / I₂ / AgCO₂CF₃ / methanol / 15 h / 20 °C

2: 95 percent / LiCl; Na₂CO₃ / Pd(dppf)Cl₂*CH₂Cl₂ / dimethylformamide / 15 h / 100 °C

3: 84 percent / ICl; AgBF₄ / methanol; tetrahydrofuran / 1 h / 20 °C

4: 100 percent / Na₂CO₃ / Pd(dppf)Cl₂*CH₂Cl₂ / ethanol; toluene / 15 h / 85 °C

5: KOH / methanol / 65 °C

With potassium hydroxide; silver tetrafluoroborate; iodine; Iodine monochloride; sodium carbonate; lithium chloride; dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH₂Cl₂; silver trifluoroacetate; In tetrahydrofuran; methanol; ethanol; N,N-dimethyl-formamide; toluene; 4: Suzuki-Miayura cross-coupling;

DOI:10.1016/S0040-4039(01)01322-3

upstream raw materials:

methyl (S)-2-[3-(2-benzyloxy-1-methylethyl)-2-(3,5-dimethyl-phenyl)-1H-pyrrolo[2,3-b]pyridin-5-yl]-2-methylpropanoate

ethyl 2-methyl-2-(pyridin-3-yl)propionate

2-methyl-2-(1-oxy-pyridin-3-yl)-propionic acid ethyl ester

2-(6-amino-pyridin-3-yl)-2-methyl-propionic acid methyl ester

Downstream raw materials:

(S)-1-(2-Azabicyclo[2.2.2]oct-2-yl)-2-[3-(2-benzyloxy-1-methylethyl)-2-(3,5-dimethylphenyl)-1H-pyrrolo[2,3-b]-pyridin-5-yl]-2-methylpropan-1-one

5-[2-(2-aza-bicyclo[2.2.2]oct-2-yl)-1,1-dimethyl-2-oxo-ethyl]-2-(3,5-dimethyl-phenyl)-3-[1-methyl-2-(2-pyridin-4-yl-ethylamino)-ethyl]-pyrrolo[2,3-b]pyridine-1-carboxylic acid tert-butyl ester

(S)-1-(2-azabicyclo[2.2.2]oct-2-yl)-2-[3-(2-benzyloxy-1-methylethyl)-2-(3,5-dimethylphenyl)-1H-1-(tert-butoxycarbonyl)pyrrolo[2,3-b]-pyridin-5-yl]-2-methylpropan-1-one

(S)-1-(2-azabicyclo[2.2.2]oct-2-yl)-2-[3-(2-hydroxy-1-methylethyl)-2-(3,5-dimethylphenyl)-1H-1-(tert-butoxycarbonyl)-pyrrolo[2,3-b]-pyridin-5-yl]-2-methylpropan-1-one

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