5-[2-(2-aza-bicyclo[2.2.2]oct-2-yl)-1,1-dimethyl-2-oxo-ethyl]-2-(3,5-dimethyl-phenyl)-3-(2-hydroxy-1-methyl-ethyl)-pyrrolo[2,3-c]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-(2-hydroxy-1-methyl-ethyl)-pyrrolo[2,3-c]pyridine-1-carboxylic acid tert-butyl ester
CAS No.:292600-34-1
Molecular Formula:C₃₄H₄₅N₃O₄
Molecular Weight:559.749
Hs Code.:

5-[2-(2-aza-bicyclo[2.2.2]oct-2-yl)-1,1-dimethyl-2-oxo-ethyl]-2-(3,5-dimethyl-phenyl)-3-(2-hydroxy-1-methyl-ethyl)-pyrrolo[2,3-<i>c</i>]pyridine-1-carboxylic acid <i>tert</i>-butyl ester

Synonyms:5-[2-(2-aza-bicyclo[2.2.2]oct-2-yl)-1,1-dimethyl-2-oxo-ethyl]-2-(3,5-dimethyl-phenyl)-3-(2-hydroxy-1-methyl-ethyl)-pyrrolo[2,3-c]pyridine-1-carboxylic acid tert-butyl ester

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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-(2-hydroxy-1-methyl-ethyl)-pyrrolo[2,3-c]pyridine-1-carboxylic acid tert-butyl ester

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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-(2-hydroxy-1-methyl-ethyl)-pyrrolo[2,3-c]pyridine-1-carboxylic acid tert-butyl ester

There total 14 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-(2-hydroxy-1-methyl-ethyl)-pyrrolo[2,3-c]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: 84.0%

: 292600-33-0
5-[2-(2-aza-bicyclo[2.2.2]oct-2-yl)-1,1-dimethyl-2-oxo-ethyl]-3-(2-benzyloxy-1-methyl-ethyl)-2-(3,5-dimethyl-phenyl)-pyrrolo[2,3-c]pyridine-1-carboxylic acid tert-butyl ester

: 292600-34-1
5-[2-(2-aza-bicyclo[2.2.2]oct-2-yl)-1,1-dimethyl-2-oxo-ethyl]-2-(3,5-dimethyl-phenyl)-3-(2-hydroxy-1-methyl-ethyl)-pyrrolo[2,3-c]pyridine-1-carboxylic acid tert-butyl ester

Guidance literature:: With hydrogen; palladium dihydroxide; In ethanol; acetic acid; at 20 ℃; for 48h; under 2585.74 Torr;
DOI:10.1016/S0040-4039(01)01322-3

Reference yield:

: 24424-99-5
di-tert-butyl dicarbonate

: 292600-34-1
5-[2-(2-aza-bicyclo[2.2.2]oct-2-yl)-1,1-dimethyl-2-oxo-ethyl]-2-(3,5-dimethyl-phenyl)-3-(2-hydroxy-1-methyl-ethyl)-pyrrolo[2,3-c]pyridine-1-carboxylic acid tert-butyl ester

Guidance literature:: Multi-step reaction with 2 steps

1: 89 percent / DMAP; K₂CO₃ / CH₂Cl₂ / 1 h / 20 °C

2: 84 percent / H₂ / Pd(OH)2/C / ethanol; acetic acid / 48 h / 20 °C / 2585.74 Torr

With dmap; hydrogen; potassium carbonate; palladium dihydroxide; In ethanol; dichloromethane; acetic acid;
DOI:10.1016/S0040-4039(01)01322-3

Reference yield:

: 5845-15-8
2-azabicyclo-[2.2.2.]octane hydrochloride

: 292600-34-1
5-[2-(2-aza-bicyclo[2.2.2]oct-2-yl)-1,1-dimethyl-2-oxo-ethyl]-2-(3,5-dimethyl-phenyl)-3-(2-hydroxy-1-methyl-ethyl)-pyrrolo[2,3-c]pyridine-1-carboxylic acid tert-butyl ester

Guidance literature:: Multi-step reaction with 8 steps

1: PyBOP; NEt₃ / CH₂Cl₂ / 15 h / 20 °C

2: 69 percent / t-BuLi; I₂ / tetrahydrofuran / -78 - -10 °C

3: 78 percent / H₂SO₄ / H₂O / 3.5 h / 95 °C

4: 62 percent / LiCl; Na₂CO₃ / Pd(dppf)Cl₂*CH₂Cl₂ / dimethylformamide / 15 h / 100 °C

5: 98 percent / IPy₂BF₄; TfOH / CH₂Cl₂ / 1.5 h / 20 °C

6: 100 percent / Na₂CO₃ / Pd(dppf)Cl₂*CH₂Cl₂ / ethanol; toluene / 15 h / 90 °C

7: 89 percent / DMAP; K₂CO₃ / CH₂Cl₂ / 1 h / 20 °C

8: 84 percent / H₂ / Pd(OH)2/C / ethanol; acetic acid / 48 h / 20 °C / 2585.74 Torr

With dmap; Barluenga reagent; trifluorormethanesulfonic acid; sulfuric acid; benzotriazol-1-yloxyl-tris-(pyrrolidino)-phosphonium hexafluorophosphate; hydrogen; iodine; tert.-butyl lithium; sodium carbonate; potassium carbonate; triethylamine; lithium chloride; palladium dihydroxide; dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH₂Cl₂; In tetrahydrofuran; ethanol; dichloromethane; water; acetic acid; N,N-dimethyl-formamide; toluene; 6: Suzuki-Miayura cross-coupling;
DOI:10.1016/S0040-4039(01)01322-3