1-bromo-5-methoxy-6-(toluene-4-sulfonyl)-5a,5b,6,6a,7,7a-hexahydro-5H-5,6,7b-triaza-cyclopropa[b]-as-indacen-4-one

Base Information

• Chemical Name: 1-bromo-5-methoxy-6-(toluene-4-sulfonyl)-5a,5b,6,6a,7,7a-hexahydro-5H-5,6,7b-triaza-cyclopropa[b]-as-indacen-4-one
• CAS No.: 890122-49-3
• Molecular Formula: C₁₈H₁₈BrN₃O₄S
• Molecular Weight: 452.329
• Mol file: 890122-49-3.mol

Synonyms:1-bromo-5-methoxy-6-(toluene-4-sulfonyl)-5a,5b,6,6a,7,7a-hexahydro-5H-5,6,7b-triaza-cyclopropa[b]-as-indacen-4-one

Chemical Property of 1-bromo-5-methoxy-6-(toluene-4-sulfonyl)-5a,5b,6,6a,7,7a-hexahydro-5H-5,6,7b-triaza-cyclopropa[b]-as-indacen-4-one

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 1-bromo-5-methoxy-6-(toluene-4-sulfonyl)-5a,5b,6,6a,7,7a-hexahydro-5H-5,6,7b-triaza-cyclopropa[b]-as-indacen-4-one

There total 6 articles about 1-bromo-5-methoxy-6-(toluene-4-sulfonyl)-5a,5b,6,6a,7,7a-hexahydro-5H-5,6,7b-triaza-cyclopropa[b]-as-indacen-4-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: 52.0%

(3aR,8bS)-8-Bromo-4-methoxy-1,3a,4,8b-tetrahydro-4,8a-diaza-as-indacen-5-one (890122-46-0) + 4-methyl-N-[(E)-phenyl-λ3-iodanylidene]benzenesulfonamide (55962-05-5) → 1-bromo-5-methoxy-6-(toluene-4-sulfonyl)-5a,5b,6,6a,7,7a-hexahydro-5H-5,6,7b-triaza-cyclopropa[b]-as-indacen-4-one (890122-49-3)

Guidance literature:

With 4 A molecular sieve; chloro[1,3-bis(2,6-di-i-propylphenyl)imidazol-2-ylidene]copper(I); In benzene; at 20 ℃; for 4h;

DOI:10.1021/ja061105q

Reference yield: 52.0%

(3aR,8bS)-8-Bromo-4-methoxy-1,3a,4,8b-tetrahydro-4,8a-diaza-as-indacen-5-one (890122-46-0) + [N-(p-tolylsulfonyl)imino]phenyliodinane (55962-05-5) → 1-bromo-5-methoxy-6-(toluene-4-sulfonyl)-5a,5b,6,6a,7,7a-hexahydro-5H-5,6,7b-triaza-cyclopropa[b]-as-indacen-4-one (890122-49-3)

Guidance literature:

With chloro[1,3-bis(2,6-di-i-propylphenyl)imidazol-2-ylidene]copper(I); In benzene; at 20 ℃; for 4h; Molecular sieve; Inert atmosphere;

DOI:10.1002/chem.200900794

Reference yield:

Carbonic acid (1R,4S)-4-(2-bromo-5-chlorocarbonyl-pyrrol-1-yl)-cyclopent-2-enyl ester tert-butyl ester → 1-bromo-5-methoxy-6-(toluene-4-sulfonyl)-5a,5b,6,6a,7,7a-hexahydro-5H-5,6,7b-triaza-cyclopropa[b]-as-indacen-4-one (890122-49-3)

Guidance literature:

Multi-step reaction with 3 steps

1: 87.7 mg / K₂CO₃ / H₂O; tetrahydrofuran; dimethylformamide / 12 h / 20 °C

2: 91.5 percent / (R,R)-1,2-bis(2'-Ph₂PPhCONH)cyclohexane; Cs₂CO₃ / Pd₂(dba)3*CHCl₃ / CH₂Cl₂ / 12 h / 20 °C

3: 52 percent / 4 Angstroem molecular sieves / N,N'-bis(2',6'-iPr₂Ph)-c-(N-CH=CH-N)C=CuCl / benzene / 4 h / 20 °C

With 4 A molecular sieve; potassium carbonate; caesium carbonate; (1R,2R)-1,2-bis[(2-diphenylphosphanyl)benzoylamino]cyclohexane; tris(dibenzylideneacetone)dipalladium⁽⁰⁾ chloroform complex; chloro[1,3-bis(2,6-di-i-propylphenyl)imidazol-2-ylidene]copper(I); In tetrahydrofuran; dichloromethane; water; N,N-dimethyl-formamide; benzene;

DOI:10.1021/ja061105q

upstream raw materials:

(3aR,8bS)-8-Bromo-4-methoxy-1,3a,4,8b-tetrahydro-4,8a-diaza-as-indacen-5-one

4-methyl-N-[(E)-phenyl-λ³-iodanylidene]benzenesulfonamide

5-bromo-1-(4-tert-butoxycarbonyloxy-cyclopent-2-enyl)-1H-pyrrole-2-carboxylic acid methyl ester

5-bromo-1-(4-tert-butoxycarbonyloxy-cyclopent-2-enyl)-1H-pyrrole-2-carboxylic acid

Downstream raw materials:

(5aS,5bR,8aR,9aS)-1-Bromo-8a-hydroxy-5-methoxy-8-methyl-6-(toluene-4-sulfonyl)-5,5a,5b,6,8,8a,9,9a-octahydro-5,6,8,9b-tetraaza-cyclopenta[b]-as-indacene-4,7-dione

N-(8-bromo-4-methoxy-2,5-dioxo-2,3,3a,4,5,8b-hexahydro-1H-4,8a-diaza-as-indacen-3-yl)-4-methyl-benzenesulfonamide

N-(8-bromo-2-hydroxy-4-methoxy-5-oxo-2,3,3a,4,5,8b-hexahydro-1H-4,8a-diaza-as-indacen-3-yl)-4-methyl-benzenesulfonamide