7-benzyloxy-5-[tert-butoxycarbonyl-(3-chloro-allyl)-amino]-4-iodo-indole-1-carboxylic acid tert-butyl ester

Base Information

• Chemical Name: 7-benzyloxy-5-[tert-butoxycarbonyl-(3-chloro-allyl)-amino]-4-iodo-indole-1-carboxylic acid tert-butyl ester
• CAS No.: 277317-31-4
• Molecular Formula: C₂₈H₃₂ClIN₂O₅
• Molecular Weight: 638.93
• Mol file: 277317-31-4.mol

Synonyms:7-benzyloxy-5-[tert-butoxycarbonyl-(3-chloro-allyl)-amino]-4-iodo-indole-1-carboxylic acid tert-butyl ester

Chemical Property of 7-benzyloxy-5-[tert-butoxycarbonyl-(3-chloro-allyl)-amino]-4-iodo-indole-1-carboxylic acid tert-butyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 7-benzyloxy-5-[tert-butoxycarbonyl-(3-chloro-allyl)-amino]-4-iodo-indole-1-carboxylic acid tert-butyl ester

There total 6 articles about 7-benzyloxy-5-[tert-butoxycarbonyl-(3-chloro-allyl)-amino]-4-iodo-indole-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: 100.0%

E/Z-1,3-Dichloropropene (542-75-6) + 1-(tert-butyloxycarbonyl)-5-[(tert-butyloxycarbonyl)amino]-7-(benzyloxy)-4-iodoindole (277317-27-8) → 7-benzyloxy-5-[tert-butoxycarbonyl-(3-chloro-allyl)-amino]-4-iodo-indole-1-carboxylic acid tert-butyl ester (277317-31-4)

Guidance literature:

With sodium hydride; In N,N-dimethyl-formamide; at 25 ℃; for 1h;

DOI:10.1021/jo000297j

Reference yield:

di-tert-butyl dicarbonate (24424-99-5) → 7-benzyloxy-5-[tert-butoxycarbonyl-(3-chloro-allyl)-amino]-4-iodo-indole-1-carboxylic acid tert-butyl ester (277317-31-4)

Guidance literature:

Multi-step reaction with 3 steps

1: 93 percent / DMAP / CH₂Cl₂ / 0.5 h / 25 °C

2: 98 percent / MeONa / methanol; CH₂Cl₂ / 0.17 h / 25 °C

3: 100 percent / NaH / dimethylformamide / 1 h / 25 °C

With dmap; sodium methylate; sodium hydride; In methanol; dichloromethane; N,N-dimethyl-formamide; 1: Acylation / 2: amide cleavage / 3: Alkylation;

DOI:10.1021/jo000297j

Reference yield:

N5,1-Dibenzoyl-5-amino-7-benzyloxyindole (124417-92-1) → 7-benzyloxy-5-[tert-butoxycarbonyl-(3-chloro-allyl)-amino]-4-iodo-indole-1-carboxylic acid tert-butyl ester (277317-31-4)

Guidance literature:

Multi-step reaction with 5 steps

1: 45 percent / N-iodosuccinimide; TsOH / tetrahydrofuran / 40 h / 25 °C

2: 99 percent / MeONa / methanol; CH₂Cl₂ / 0.17 h / 25 °C

3: 93 percent / DMAP / CH₂Cl₂ / 0.5 h / 25 °C

4: 98 percent / MeONa / methanol; CH₂Cl₂ / 0.17 h / 25 °C

5: 100 percent / NaH / dimethylformamide / 1 h / 25 °C

With dmap; N-iodo-succinimide; sodium methylate; sodium hydride; toluene-4-sulfonic acid; In tetrahydrofuran; methanol; dichloromethane; N,N-dimethyl-formamide; 1: Iodination / 2: amide cleavage / 3: Acylation / 4: amide cleavage / 5: Alkylation;

DOI:10.1021/jo000297j

upstream raw materials:

E/Z-1,3-Dichloropropene

1-(tert-butyloxycarbonyl)-5-[(tert-butyloxycarbonyl)amino]-7-(benzyloxy)-4-iodoindole

di-tert-butyl dicarbonate

N⁵,1-Dibenzoyl-5-amino-7-benzyloxyindole

Downstream raw materials:

5-(benzyloxy)-1-(chloromethyl)-1,2-dihydro-3-[(1H-indol-2-yl)carbonyl]-3H-pyrrolo[3,2-e]indole

5-(benzyloxy)-1-(chloromethyl)-1,2-dihydro-3-[(5-methoxy-1H-indol-2-yl)carbonyl]-3H-pyrrolo[3,2-e]indole

5-(benzyloxy)-1-(chloromethyl)-1,2-dihydro-3-[(5,6,7-trimethoxy-1H-indol-2-yl)carbonyl]-3H-pyrrolo[3,2-e]indole

5-(benzyloxy)-1-(chloromethyl)-1,2-dihydro-3-[(3-carbamoyl-1,2-dihydro-3H-pyrrolo[3,2-e]indol-7-yl)carbonyl]-3H-pyrrolo[3,2-e]indole