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

Base Information

• Chemical Name: 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
• CAS No.: 385449-78-5
• Molecular Formula: C₄₁H₅₃N₅O₃
• Molecular Weight: 663.904
• Mol file: 385449-78-5.mol

Synonyms: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

Chemical Property of 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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 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

There total 18 articles about 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 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:

5-[2-(2-aza-bicyclo[2.2.2]oct-2-yl)-1,1-dimethyl-2-oxo-ethyl]-2-(3,5-dimethyl-phenyl)-3-{2-[(3,5-dinitro-benzenesulfonyl)-(2-pyridin-4-yl-ethyl)-amino]-1-methyl-ethyl}-pyrrolo[2,3-b]pyridine-1-carboxylic acid tert-butyl ester → 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 (385449-78-5)

Guidance literature:

With propylamine; In dichloromethane; at 20 ℃; for 0.25h;

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

Reference yield:

2-azabicyclo-[2.2.2.]octane hydrochloride (5845-15-8) → 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 (385449-78-5)

Guidance literature:

Multi-step reaction with 8 steps

1: PyBOP; NEt₃ / CH₂Cl₂ / 4 h / 20 °C

2: 84 percent / DMAP; K₂CO₃ / CH₂Cl₂ / 5 h / 20 °C

3: 92 percent / H₂ / Pd(OH)2/C / ethanol; acetic acid / 72 h / 20 °C / 2585.74 Torr

4: Zn(N₃)2*2Py; PPh₃; imidazole / DEAD / CH₂Cl₂ / 15 h / 0 - 15 °C

5: H₂ / Pd(OH)2/C / ethanol / 15 h / 20 °C / 2585.74 Torr

6: 79 percent / NaHCO₃ / H₂O; CH₂Cl₂ / 0.5 h / 20 °C

7: DEAD / benzene / 1 h / 20 °C

8: n-PrNH₂ / CH₂Cl₂ / 0.25 h / 20 °C

With 1H-imidazole; propylamine; dmap; zinc azide * 2 pyridine; benzotriazol-1-yloxyl-tris-(pyrrolidino)-phosphonium hexafluorophosphate; hydrogen; sodium hydrogencarbonate; potassium carbonate; triethylamine; triphenylphosphine; diethylazodicarboxylate; palladium dihydroxide; diethylazodicarboxylate; In ethanol; dichloromethane; water; acetic acid; benzene;

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

Reference yield:

2-methyl-2-(1-oxy-pyridin-3-yl)-propionic acid ethyl ester (169253-21-8) → 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 (385449-78-5)

Guidance literature:

Multi-step reaction with 16 steps

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

2: 88 percent / HCl / 8 h / 100 °C

3: 100 percent / H₂SO₄ / 15 h / 65 °C

4: 62 percent / I₂ / AgCO₂CF₃ / methanol / 15 h / 20 °C

5: 95 percent / LiCl; Na₂CO₃ / Pd(dppf)Cl₂*CH₂Cl₂ / dimethylformamide / 15 h / 100 °C

6: 84 percent / ICl; AgBF₄ / methanol; tetrahydrofuran / 1 h / 20 °C

7: 100 percent / Na₂CO₃ / Pd(dppf)Cl₂*CH₂Cl₂ / ethanol; toluene / 15 h / 85 °C

8: KOH / methanol / 65 °C

9: PyBOP; NEt₃ / CH₂Cl₂ / 4 h / 20 °C

10: 84 percent / DMAP; K₂CO₃ / CH₂Cl₂ / 5 h / 20 °C

11: 92 percent / H₂ / Pd(OH)2/C / ethanol; acetic acid / 72 h / 20 °C / 2585.74 Torr

12: Zn(N₃)2*2Py; PPh₃; imidazole / DEAD / CH₂Cl₂ / 15 h / 0 - 15 °C

13: H₂ / Pd(OH)2/C / ethanol / 15 h / 20 °C / 2585.74 Torr

14: 79 percent / NaHCO₃ / H₂O; CH₂Cl₂ / 0.5 h / 20 °C

15: DEAD / benzene / 1 h / 20 °C

16: n-PrNH₂ / CH₂Cl₂ / 0.25 h / 20 °C

With 1H-imidazole; propylamine; dmap; potassium hydroxide; silver tetrafluoroborate; zinc azide * 2 pyridine; sulfuric acid; benzotriazol-1-yloxyl-tris-(pyrrolidino)-phosphonium hexafluorophosphate; hydrogen; iodine; Iodine monochloride; sodium hydrogencarbonate; sodium carbonate; potassium carbonate; triethylamine; triphenylphosphine; lithium chloride; diethylazodicarboxylate; hydrogenchloride; palladium dihydroxide; dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH₂Cl₂; silver trifluoroacetate; diethylazodicarboxylate; In tetrahydrofuran; methanol; ethanol; dichloromethane; water; acetic acid; 1,2-dichloro-ethane; N,N-dimethyl-formamide; toluene; benzene; 7: Suzuki-Miayura cross-coupling;

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

upstream raw materials:

2-azabicyclo-[2.2.2.]octane hydrochloride

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