5-[2-(7-azabicyclo[2.2.1]hept-7-yl)-1,1-dimethyl-2-oxoethyl]-3-[(1S)-2-(benzyloxy)-1-methylethyl]-2-iodo-1H-indole

Base Information

• Chemical Name: 5-[2-(7-azabicyclo[2.2.1]hept-7-yl)-1,1-dimethyl-2-oxoethyl]-3-[(1S)-2-(benzyloxy)-1-methylethyl]-2-iodo-1H-indole
• CAS No.: 357193-12-5
• Molecular Formula: C₂₈H₃₃IN₂O₂
• Molecular Weight: 556.487

Synonyms:5-[2-(7-azabicyclo[2.2.1]hept-7-yl)-1,1-dimethyl-2-oxoethyl]-3-[(1S)-2-(benzyloxy)-1-methylethyl]-2-iodo-1H-indole

Chemical Property of 5-[2-(7-azabicyclo[2.2.1]hept-7-yl)-1,1-dimethyl-2-oxoethyl]-3-[(1S)-2-(benzyloxy)-1-methylethyl]-2-iodo-1H-indole

Chemical Property:

Purity/Quality:

Safty Information:

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Technology Process of 5-[2-(7-azabicyclo[2.2.1]hept-7-yl)-1,1-dimethyl-2-oxoethyl]-3-[(1S)-2-(benzyloxy)-1-methylethyl]-2-iodo-1H-indole

There total 10 articles about 5-[2-(7-azabicyclo[2.2.1]hept-7-yl)-1,1-dimethyl-2-oxoethyl]-3-[(1S)-2-(benzyloxy)-1-methylethyl]-2-iodo-1H-indole 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: 92.0%

5-[2-(7-azabicyclo[2.2.1]hept-7-yl)-1,1-dimethyl-2-oxoethyl]-3-[(1S)-2-(benzyloxy)-1-methylethyl]-2-(triethylsilyl)-1H-indole (357193-25-0) → 5-[2-(7-azabicyclo[2.2.1]hept-7-yl)-1,1-dimethyl-2-oxoethyl]-3-[(1S)-2-(benzyloxy)-1-methylethyl]-2-iodo-1H-indole (357193-12-5)

Guidance literature:

With silver tetrafluoroborate; Iodine monochloride; In tetrahydrofuran; methanol; at 0 ℃; for 0.25h;

DOI:10.1016/S0040-4020(01)00367-2

Reference yield:

ethyl 2-methyl-2-(4-nitrophenyl)propanoate (83397-45-9) → 5-[2-(7-azabicyclo[2.2.1]hept-7-yl)-1,1-dimethyl-2-oxoethyl]-3-[(1S)-2-(benzyloxy)-1-methylethyl]-2-iodo-1H-indole (357193-12-5)

Guidance literature:

Multi-step reaction with 6 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

With sodium hydroxide; silver tetrafluoroborate; oxalyl dichloride; hydrogen; Iodine monochloride; potassium carbonate; N,N-dimethyl-formamide; triphenylphosphine; calcium carbonate; lithium chloride; palladium diacetate; palladium on activated charcoal; In tetrahydrofuran; methanol; ethanol; water; N,N-dimethyl-formamide; toluene; 5.1: Larock reaction;

DOI:10.1016/S0040-4020(01)00367-2

Reference yield:

O-benzyl 2,2,2-trichloroacetimidate (81927-55-1) → 5-[2-(7-azabicyclo[2.2.1]hept-7-yl)-1,1-dimethyl-2-oxoethyl]-3-[(1S)-2-(benzyloxy)-1-methylethyl]-2-iodo-1H-indole (357193-12-5)

Guidance literature:

Multi-step reaction with 7 steps

1.1: 74 percent / CF₃SO₃H / cyclohexane; CCl₄ / 16 h / 20 °C

2.1: 89 percent / LiAlH₄ / tetrahydrofuran / 4 h / 20 °C

3.1: oxalyl chloride; DMSO; i-Pr₂NEt / CH₂Cl₂ / -78 - -15 °C

4.1: 46.54 g / PPh₃ / CH₂Cl₂ / 0 - 20 °C

5.1: n-BuLi / tetrahydrofuran; hexane / 2 h / -78 - 20 °C

5.2: 94 percent / tetrahydrofuran; hexane / 1 h / 0 - 10 °C

6.1: 72 percent / K₂CO₃; LiCl; PPh₃ / Pd(OAc)2 / dimethylformamide / 16 h / 100 °C

7.1: 92 percent / AgBF₄; ICl / methanol; tetrahydrofuran / 0.25 h / 0 °C

With lithium aluminium tetrahydride; silver tetrafluoroborate; n-butyllithium; oxalyl dichloride; trifluorormethanesulfonic acid; Iodine monochloride; potassium carbonate; dimethyl sulfoxide; N-ethyl-N,N-diisopropylamine; triphenylphosphine; lithium chloride; palladium diacetate; In tetrahydrofuran; methanol; tetrachloromethane; hexane; dichloromethane; cyclohexane; N,N-dimethyl-formamide; 3.1: Swern-Moffat oxidation / 6.1: Larock reaction;

DOI:10.1016/S0040-4020(01)00367-2

upstream raw materials:

5-[2-(7-azabicyclo[2.2.1]hept-7-yl)-1,1-dimethyl-2-oxoethyl]-3-[(1S)-2-(benzyloxy)-1-methylethyl]-2-(triethylsilyl)-1H-indole

ethyl 2-methyl-2-(4-nitrophenyl)propanoate

(S)-3-benzyloxy-2-methylpropan-1-ol

O-benzyl 2,2,2-trichloroacetimidate

Downstream raw materials:

tert-butyl 5-[2-(7-azabicyclo[2.2.1]hept-7-yl)-1,1-dimethyl-2-oxoethyl]-3-[(1S)-2-{[(2,4-dinitrophenyl)sulfonyl]amino}-1-methylethyl]-2-(3,4,5-trimethylphenyl)-1H-indole-1-carboxylate

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

tert-butyl 5-[2-(7-azabicyclo[2.2.1]hept-7-yl)-1,1-dimethyl-2-oxoethyl]-3-[(1S)-2-(benzyloxy)-1-methylethyl]-2-(3,4,5-trimethylphenyl)-1H-indole-1-carboxylate

tert-butyl 5-[2-(7-azabicyclo[2.2.1]hept-7-yl)-1,1-dimethyl-2-oxoethyl]-3-[(1S)-2-azido-1-methylethyl]-2-(3,4,5-trimethylphenyl)-1H-indole-1-carboxylate

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