(S)-1-(2-Azabicyclo[2.2.2]oct-2-yl)-2-[3-(2-benzyloxy-1-methylethyl)-2-triethylsilyl-1H-pyrrolo[2,3-c]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-triethylsilyl-1H-pyrrolo[2,3-c]pyridin-5-yl]-2-methylpropan-1-one
CAS No.:292600-30-7
Molecular Formula:C₃₄H₄₉N₃O₂Si
Molecular Weight:559.867
Hs Code.:

Synonyms:(S)-1-(2-Azabicyclo[2.2.2]oct-2-yl)-2-[3-(2-benzyloxy-1-methylethyl)-2-triethylsilyl-1H-pyrrolo[2,3-c]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-triethylsilyl-1H-pyrrolo[2,3-c]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-triethylsilyl-1H-pyrrolo[2,3-c]pyridin-5-yl]-2-methylpropan-1-one

There total 9 articles about (S)-1-(2-Azabicyclo[2.2.2]oct-2-yl)-2-[3-(2-benzyloxy-1-methylethyl)-2-triethylsilyl-1H-pyrrolo[2,3-c]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: 62.0%

: Pd(dppf)Cl2·CH2Cl2

: 246219-83-0
(S)-(4-benzyloxy-3-methylbut-1-ynyl)triethylsilane

: 292600-29-4
2-(5-amino-4-iodopyridin-2-yl)-1-(2-azabicyclo[2.2.2]oct-2-yl)-2-methylpropan-1-one

: 292600-30-7
(S)-1-(2-Azabicyclo[2.2.2]oct-2-yl)-2-[3-(2-benzyloxy-1-methylethyl)-2-triethylsilyl-1H-pyrrolo[2,3-c]pyridin-5-yl]-2-methylpropan-1-one

Guidance literature:: With sodium carbonate; lithium chloride; In N,N-dimethyl-formamide;

Reference yield: 62.0%

: 246219-83-0
(S)-(4-benzyloxy-3-methylbut-1-ynyl)triethylsilane

: 292600-29-4
2-(5-amino-4-iodopyridin-2-yl)-1-(2-azabicyclo[2.2.2]oct-2-yl)-2-methylpropan-1-one

: 292600-30-7
(S)-1-(2-Azabicyclo[2.2.2]oct-2-yl)-2-[3-(2-benzyloxy-1-methylethyl)-2-triethylsilyl-1H-pyrrolo[2,3-c]pyridin-5-yl]-2-methylpropan-1-one

Guidance literature:: With sodium carbonate; lithium chloride; dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH₂Cl₂; In N,N-dimethyl-formamide; at 100 ℃; for 15h;
DOI:10.1016/S0040-4039(01)01322-3

Reference yield:

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

: 292600-30-7
(S)-1-(2-Azabicyclo[2.2.2]oct-2-yl)-2-[3-(2-benzyloxy-1-methylethyl)-2-triethylsilyl-1H-pyrrolo[2,3-c]pyridin-5-yl]-2-methylpropan-1-one

Guidance literature:: Multi-step reaction with 4 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

With sulfuric acid; benzotriazol-1-yloxyl-tris-(pyrrolidino)-phosphonium hexafluorophosphate; iodine; tert.-butyl lithium; sodium carbonate; triethylamine; lithium chloride; dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH₂Cl₂; In tetrahydrofuran; dichloromethane; water; N,N-dimethyl-formamide;
DOI:10.1016/S0040-4039(01)01322-3