tert-butyl 5-[2-(7-azabicyclo[2.2.1]hept-7-yl)-1,1-dimethyl-2-oxoethyl]-3-[(1S)-1-methyl-2-[(2-pyridin-4-ylethyl)amino]ethyl]-2-(3,4,5-trimethylphenyl)-1H-indole-1-carboxylate

Base Information

Chemical Name:tert-butyl 5-[2-(7-azabicyclo[2.2.1]hept-7-yl)-1,1-dimethyl-2-oxoethyl]-3-[(1S)-1-methyl-2-[(2-pyridin-4-ylethyl)amino]ethyl]-2-(3,4,5-trimethylphenyl)-1H-indole-1-carboxylate
CAS No.:357193-23-8
Molecular Formula:C₄₂H₅₄N₄O₃
Molecular Weight:662.916
Hs Code.:

tert-butyl 5-[2-(7-azabicyclo[2.2.1]hept-7-yl)-1,1-dimethyl-2-oxoethyl]-3-[(1S)-1-methyl-2-[(2-pyridin-4-ylethyl)amino]ethyl]-2-(3,4,5-trimethylphenyl)-1H-indole-1-carboxylate

Synonyms:tert-butyl 5-[2-(7-azabicyclo[2.2.1]hept-7-yl)-1,1-dimethyl-2-oxoethyl]-3-[(1S)-1-methyl-2-[(2-pyridin-4-ylethyl)amino]ethyl]-2-(3,4,5-trimethylphenyl)-1H-indole-1-carboxylate

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Chemical Property of tert-butyl 5-[2-(7-azabicyclo[2.2.1]hept-7-yl)-1,1-dimethyl-2-oxoethyl]-3-[(1S)-1-methyl-2-[(2-pyridin-4-ylethyl)amino]ethyl]-2-(3,4,5-trimethylphenyl)-1H-indole-1-carboxylate

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Technology Process of tert-butyl 5-[2-(7-azabicyclo[2.2.1]hept-7-yl)-1,1-dimethyl-2-oxoethyl]-3-[(1S)-1-methyl-2-[(2-pyridin-4-ylethyl)amino]ethyl]-2-(3,4,5-trimethylphenyl)-1H-indole-1-carboxylate

There total 19 articles about tert-butyl 5-[2-(7-azabicyclo[2.2.1]hept-7-yl)-1,1-dimethyl-2-oxoethyl]-3-[(1S)-1-methyl-2-[(2-pyridin-4-ylethyl)amino]ethyl]-2-(3,4,5-trimethylphenyl)-1H-indole-1-carboxylate 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-(7-aza-bicyclo[2.2.1]hept-7-yl)-1,1-dimethyl-2-oxo-ethyl]-3-{2-[(2,4-dinitro-benzenesulfonyl)-(2-pyridin-4-yl-ethyl)-amino]-1-methyl-ethyl}-2-(3,4,5-trimethyl-phenyl)-indole-1-carboxylic acid tert-butyl ester

: 357193-23-8
tert-butyl 5-[2-(7-azabicyclo[2.2.1]hept-7-yl)-1,1-dimethyl-2-oxoethyl]-3-[(1S)-1-methyl-2-[(2-pyridin-4-ylethyl)amino]ethyl]-2-(3,4,5-trimethylphenyl)-1H-indole-1-carboxylate

Guidance literature:: With propylamine; In dichloromethane; at 20 ℃; for 0.5h;
DOI:10.1016/S0040-4020(01)00367-2

Reference yield:

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

: 357193-23-8
tert-butyl 5-[2-(7-azabicyclo[2.2.1]hept-7-yl)-1,1-dimethyl-2-oxoethyl]-3-[(1S)-1-methyl-2-[(2-pyridin-4-ylethyl)amino]ethyl]-2-(3,4,5-trimethylphenyl)-1H-indole-1-carboxylate

Guidance literature:: Multi-step reaction with 7 steps

1: DMAP / CH₂Cl₂ / 2 h / 20 °C

2: 2.155 g / H₂ / 10 percent Pd/C / ethanol / 3 h / 20 °C / 2068.59 Torr

3: 90 percent / Zn(N₃)2*2Pyr; DEAD; PPh₃ / imidazole / CH₂Cl₂ / 24 h / 20 °C

4: 95 percent / H₂ / 10 percent Pd/C / ethanol / 15 h / 20 °C / 760 Torr

5: 93 percent / NaHCO₃ / CH₂Cl₂; H₂O / 0.5 h / 0 - 20 °C

6: DEAD; PPh₃ / benzene / 1 h / 20 °C

7: 0.334 g / n-PrNH₂ / CH₂Cl₂ / 0.5 h / 20 °C

With propylamine; dmap; Zn(N₃)2/bis-pyridine complex; hydrogen; sodium hydrogencarbonate; triphenylphosphine; diethylazodicarboxylate; 1H-imidazole; palladium on activated charcoal; In ethanol; dichloromethane; water; benzene;
DOI:10.1016/S0040-4020(01)00367-2

Reference yield:

: 83397-45-9
ethyl 2-methyl-2-(4-nitrophenyl)propanoate

: 357193-23-8
tert-butyl 5-[2-(7-azabicyclo[2.2.1]hept-7-yl)-1,1-dimethyl-2-oxoethyl]-3-[(1S)-1-methyl-2-[(2-pyridin-4-ylethyl)amino]ethyl]-2-(3,4,5-trimethylphenyl)-1H-indole-1-carboxylate

Guidance literature:: Multi-step reaction with 14 steps

1.1: 97 percent / NaOH / methanol / 4 h / 60 °C

2.1: (COCl)2; DMF / toluene / 80 °C

2.2: 96 percent / Et₃N / CH₂Cl₂ / 12 h / 20 °C

3.1: 100 percent / H₂ / 10 percent Pd/C / ethanol / 1 h / 20 °C / 2327.17 Torr

4.1: 97 percent / CaCO₃; ICl / methanol; H₂O / 0.5 h / 20 °C

5.1: 72 percent / K₂CO₃; LiCl; PPh₃ / Pd(OAc)2 / dimethylformamide / 16 h / 100 °C

6.1: 92 percent / AgBF₄; ICl / methanol; tetrahydrofuran / 0.25 h / 0 °C

7.1: 96 percent / 2M Na₂CO₃ / (dppf)PdCl₂*CH₂Cl₂ / toluene; ethanol / 15 h / 80 °C

8.1: DMAP / CH₂Cl₂ / 2 h / 20 °C

9.1: 2.155 g / H₂ / 10 percent Pd/C / ethanol / 3 h / 20 °C / 2068.59 Torr

10.1: 90 percent / Zn(N₃)2*2Pyr; DEAD; PPh₃ / imidazole / CH₂Cl₂ / 24 h / 20 °C

11.1: 95 percent / H₂ / 10 percent Pd/C / ethanol / 15 h / 20 °C / 760 Torr

12.1: 93 percent / NaHCO₃ / CH₂Cl₂; H₂O / 0.5 h / 0 - 20 °C

13.1: DEAD; PPh₃ / benzene / 1 h / 20 °C

14.1: 0.334 g / n-PrNH₂ / CH₂Cl₂ / 0.5 h / 20 °C

With propylamine; dmap; sodium hydroxide; silver tetrafluoroborate; oxalyl dichloride; Zn(N₃)2/bis-pyridine complex; hydrogen; Iodine monochloride; sodium hydrogencarbonate; sodium carbonate; potassium carbonate; N,N-dimethyl-formamide; triphenylphosphine; calcium carbonate; lithium chloride; diethylazodicarboxylate; 1H-imidazole; palladium diacetate; palladium on activated charcoal; dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH₂Cl₂; In tetrahydrofuran; methanol; ethanol; dichloromethane; water; N,N-dimethyl-formamide; toluene; benzene; 5.1: Larock reaction;
DOI:10.1016/S0040-4020(01)00367-2