(E)-2-(1-(bromomethyl)-3-(3-(4-(2-morpholinoethoxy)phenyl)acryloyl)-5-nitro-2,3-dihydro-1H-benzo[e]indole-7-sulfonamido)ethyl di-tert-butyl phosphate

Base Information

• Chemical Name: (E)-2-(1-(bromomethyl)-3-(3-(4-(2-morpholinoethoxy)phenyl)acryloyl)-5-nitro-2,3-dihydro-1H-benzo[e]indole-7-sulfonamido)ethyl di-tert-butyl phosphate
• CAS No.: 1345690-17-6
• Molecular Formula: C₃₈H₅₀BrN₄O₁₁PS
• Molecular Weight: 881.779

Synonyms:(E)-2-(1-(bromomethyl)-3-(3-(4-(2-morpholinoethoxy)phenyl)acryloyl)-5-nitro-2,3-dihydro-1H-benzo[e]indole-7-sulfonamido)ethyl di-tert-butyl phosphate

Chemical Property of (E)-2-(1-(bromomethyl)-3-(3-(4-(2-morpholinoethoxy)phenyl)acryloyl)-5-nitro-2,3-dihydro-1H-benzo[e]indole-7-sulfonamido)ethyl di-tert-butyl phosphate

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Technology Process of (E)-2-(1-(bromomethyl)-3-(3-(4-(2-morpholinoethoxy)phenyl)acryloyl)-5-nitro-2,3-dihydro-1H-benzo[e]indole-7-sulfonamido)ethyl di-tert-butyl phosphate

There total 11 articles about (E)-2-(1-(bromomethyl)-3-(3-(4-(2-morpholinoethoxy)phenyl)acryloyl)-5-nitro-2,3-dihydro-1H-benzo[e]indole-7-sulfonamido)ethyl di-tert-butyl phosphate 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: 50.0%

(E)-3-(4-(2-morpholinoethoxy)phenyl)acrylic acid hydrobromide (1354943-63-7) + 2-(1-(bromomethyl)-5-nitro-2,3-dihydro-1H-benzo[e]indole-7-sulfonamido)ethyl di-tert-butyl phosphate (1214876-60-4) → (E)-2-(1-(bromomethyl)-3-(3-(4-(2-morpholinoethoxy)phenyl)acryloyl)-5-nitro-2,3-dihydro-1H-benzo[e]indole-7-sulfonamido)ethyl di-tert-butyl phosphate (1345690-17-6)

Guidance literature:

With EDCI*HBr; toluene-4-sulfonic acid; In dichloromethane; N,N-dimethyl acetamide; for 3h;

DOI:10.1016/j.bmc.2011.08.045

Reference yield:

1-(1-(bromomethyl)-1H-benzo[e]indol-3(2H)-yl)-2,2,2-trifluoroethanone (1214876-53-5) → (E)-2-(1-(bromomethyl)-3-(3-(4-(2-morpholinoethoxy)phenyl)acryloyl)-5-nitro-2,3-dihydro-1H-benzo[e]indole-7-sulfonamido)ethyl di-tert-butyl phosphate (1345690-17-6)

Guidance literature:

Multi-step reaction with 6 steps

1: chlorosulfonic acid / dichloromethane / 7 h / -78 - 5 °C

2: oxalyl dichloride / dichloromethane; N,N-dimethyl-formamide / 1 h / 0 °C

3: sulfuric acid; potassium nitrate / 0.25 h / 0 °C

4: N-ethyl-N,N-diisopropylamine / dichloromethane / 0.5 h / -50 °C

5: methanol; caesium carbonate / dichloromethane; water / 0.25 h / -10 °C

6: EDCI*HBr; toluene-4-sulfonic acid / dichloromethane; N,N-dimethyl acetamide / 3 h

With methanol; chlorosulfonic acid; oxalyl dichloride; sulfuric acid; EDCI*HBr; caesium carbonate; toluene-4-sulfonic acid; potassium nitrate; N-ethyl-N,N-diisopropylamine; In dichloromethane; N,N-dimethyl acetamide; water; N,N-dimethyl-formamide;

DOI:10.1016/j.bmc.2011.08.045

Reference yield:

C15H11BrF3NO4S → (E)-2-(1-(bromomethyl)-3-(3-(4-(2-morpholinoethoxy)phenyl)acryloyl)-5-nitro-2,3-dihydro-1H-benzo[e]indole-7-sulfonamido)ethyl di-tert-butyl phosphate (1345690-17-6)

Guidance literature:

Multi-step reaction with 5 steps

1: oxalyl dichloride / dichloromethane; N,N-dimethyl-formamide / 1 h / 0 °C

2: sulfuric acid; potassium nitrate / 0.25 h / 0 °C

3: N-ethyl-N,N-diisopropylamine / dichloromethane / 0.5 h / -50 °C

4: methanol; caesium carbonate / dichloromethane; water / 0.25 h / -10 °C

5: EDCI*HBr; toluene-4-sulfonic acid / dichloromethane; N,N-dimethyl acetamide / 3 h

With methanol; oxalyl dichloride; sulfuric acid; EDCI*HBr; caesium carbonate; toluene-4-sulfonic acid; potassium nitrate; N-ethyl-N,N-diisopropylamine; In dichloromethane; N,N-dimethyl acetamide; water; N,N-dimethyl-formamide;

DOI:10.1016/j.bmc.2011.08.045

upstream raw materials:

1-(1-(chloromethyl)-1H-benzo[e]indol-3(2H)-yl)-2,2,2-trifluoroethanone

2-aminoethyl di(tert-butyl) phosphate

1-(bromomethyl)-5-nitro-3-(2,2,2-trifluoroacetyl)-2,3-dihydro-1H-benzo[e]indole-7-sulfonyl chloride

(3-(2,2,2-trifluoroacetyl)-2,3-dihydro-1H-benzo[e]indol-1-yl)-methyl methanesulfonate

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