(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

Base Information

Chemical Name:(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
CAS No.:246231-08-3
Molecular Formula:C₄₁H₅₁N₃O₄
Molecular Weight:649.874
Hs Code.:

(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

Synonyms:(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

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Chemical Property of (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

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Technology Process of (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

There total 12 articles about (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 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: 90.0%

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

: 246231-07-2
(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

: 246231-08-3
(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

Guidance literature:: With dmap; potassium carbonate; In dichloromethane;

Reference yield:

: 169253-21-8
2-methyl-2-(1-oxy-pyridin-3-yl)-propionic acid ethyl ester

: 246231-08-3
(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

Guidance literature:: Multi-step reaction with 10 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

With dmap; potassium hydroxide; silver tetrafluoroborate; sulfuric acid; benzotriazol-1-yloxyl-tris-(pyrrolidino)-phosphonium hexafluorophosphate; iodine; Iodine monochloride; sodium carbonate; potassium carbonate; triethylamine; lithium chloride; hydrogenchloride; dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH₂Cl₂; silver trifluoroacetate; In tetrahydrofuran; methanol; ethanol; dichloromethane; 1,2-dichloro-ethane; N,N-dimethyl-formamide; toluene; 7: Suzuki-Miayura cross-coupling;
DOI:10.1016/S0040-4039(01)01322-3

Reference yield:

: 120690-70-2
ethyl 2-methyl-2-(pyridin-3-yl)propionate

: 246231-08-3
(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

Guidance literature:: Multi-step reaction with 11 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

10: PyBOP; NEt₃ / CH₂Cl₂ / 4 h / 20 °C

11: 84 percent / DMAP; K₂CO₃ / CH₂Cl₂ / 5 h / 20 °C

With dmap; potassium hydroxide; silver tetrafluoroborate; sulfuric acid; benzotriazol-1-yloxyl-tris-(pyrrolidino)-phosphonium hexafluorophosphate; iodine; Iodine monochloride; sodium hydrogencarbonate; sodium carbonate; potassium carbonate; triethylamine; 3-chloro-benzenecarboperoxoic acid; lithium chloride; hydrogenchloride; dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH₂Cl₂; silver trifluoroacetate; In tetrahydrofuran; methanol; ethanol; dichloromethane; chloroform; water; 1,2-dichloro-ethane; N,N-dimethyl-formamide; toluene; 8: Suzuki-Miayura cross-coupling;
DOI:10.1016/S0040-4039(01)01322-3