(5-Benzyloxy-1-hydroxymethyl-8-methyl-1,6-dihydro-2H-pyrrolo[3,2-e]indol-3-yl)-(5-methoxy-1H-indol-2-yl)-methanone

Base Information

• Chemical Name: (5-Benzyloxy-1-hydroxymethyl-8-methyl-1,6-dihydro-2H-pyrrolo[3,2-e]indol-3-yl)-(5-methoxy-1H-indol-2-yl)-methanone
• CAS No.: 101134-49-0
• Molecular Formula: C₂₉H₂₇N₃O₄
• Molecular Weight: 481.551

Synonyms:(5-Benzyloxy-1-hydroxymethyl-8-methyl-1,6-dihydro-2H-pyrrolo[3,2-e]indol-3-yl)-(5-methoxy-1H-indol-2-yl)-methanone

Chemical Property of (5-Benzyloxy-1-hydroxymethyl-8-methyl-1,6-dihydro-2H-pyrrolo[3,2-e]indol-3-yl)-(5-methoxy-1H-indol-2-yl)-methanone

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
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MSDS Files:

Useful:

Technology Process of (5-Benzyloxy-1-hydroxymethyl-8-methyl-1,6-dihydro-2H-pyrrolo[3,2-e]indol-3-yl)-(5-methoxy-1H-indol-2-yl)-methanone

There total 13 articles about (5-Benzyloxy-1-hydroxymethyl-8-methyl-1,6-dihydro-2H-pyrrolo[3,2-e]indol-3-yl)-(5-methoxy-1H-indol-2-yl)-methanone 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:

3-nitro-4-chlorophenol (610-78-6) → (5-Benzyloxy-1-hydroxymethyl-8-methyl-1,6-dihydro-2H-pyrrolo[3,2-e]indol-3-yl)-(5-methoxy-1H-indol-2-yl)-methanone (101134-49-0)

Guidance literature:

Multi-step reaction with 12 steps

1: 96 percent / K₂CO₃ / acetone; dimethylformamide / 64 h / Ambient temperature

2: 77 percent / NaH / dimethylsulfoxide / 24 h / 105 - 115 °C

3: 40 percent / diisobutylaluminum hydride / tetrahydrofuran / 2.3 h / Ambient temperature

4: 69 percent / hydrogen / 84.5percent PtO₂ / ethanol / 2.75 h / 2327.2 Torr

5: 111 g / pyridine / 1.42 h / 5 °C

6: 1.) sodium acetate, 2.) triethylamine / 1.) ethanol, reflux, 20 h, 2.) methylene chloride

7: 64 percent / nitric acid / nitromethane / 0.67 h / 0 °C

8: 81 percent / hydrogen / 84.5percent PtO₂ / tetrahydrofuran; ethanol / 2 h / 2068.6 Torr

9: 1.) sulfuryl chloride, 2.) 1,8-bis(dimethylamino)naphthalene / 1.) methylene chloride, -70 deg C, 45 min, 2.) -70 deg C, 4 h

10: 90 percent / borane-methyl sulfide, 4-Angstroem molecular sieves / tetrahydrofuran / 3 h / Heating

11: sodium bis(2-methoxyethoxy)aluminum hydride / tetrahydrofuran; toluene

12: 1-ethyl-3-<3-(dimethylamino)propyl>carbodiimide hydrochloride

With pyridine; sulfuryl dichloride; dimethylsulfide borane complex; 4 A molecular sieve; hydrogen; nitric acid; sodium acetate; N,N,N',N'-tetramethyl-1,8-diaminonaphthalene; sodium hydride; diisobutylaluminium hydride; potassium carbonate; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine; sodium bis(2-methoxyethoxy)aluminium dihydride; platinum(IV) oxide; In tetrahydrofuran; nitromethane; ethanol; dimethyl sulfoxide; N,N-dimethyl-formamide; acetone; toluene;

DOI:10.1021/jm00398a017

Reference yield:

2-[4-(benzyloxy)-2-nitrophenyl]propane-1,3-diol (106014-83-9) → (5-Benzyloxy-1-hydroxymethyl-8-methyl-1,6-dihydro-2H-pyrrolo[3,2-e]indol-3-yl)-(5-methoxy-1H-indol-2-yl)-methanone (101134-49-0)

Guidance literature:

Multi-step reaction with 9 steps

1: 69 percent / hydrogen / 84.5percent PtO₂ / ethanol / 2.75 h / 2327.2 Torr

2: 111 g / pyridine / 1.42 h / 5 °C

3: 1.) sodium acetate, 2.) triethylamine / 1.) ethanol, reflux, 20 h, 2.) methylene chloride

4: 64 percent / nitric acid / nitromethane / 0.67 h / 0 °C

5: 81 percent / hydrogen / 84.5percent PtO₂ / tetrahydrofuran; ethanol / 2 h / 2068.6 Torr

6: 1.) sulfuryl chloride, 2.) 1,8-bis(dimethylamino)naphthalene / 1.) methylene chloride, -70 deg C, 45 min, 2.) -70 deg C, 4 h

7: 90 percent / borane-methyl sulfide, 4-Angstroem molecular sieves / tetrahydrofuran / 3 h / Heating

8: sodium bis(2-methoxyethoxy)aluminum hydride / tetrahydrofuran; toluene

9: 1-ethyl-3-<3-(dimethylamino)propyl>carbodiimide hydrochloride

With pyridine; sulfuryl dichloride; dimethylsulfide borane complex; 4 A molecular sieve; hydrogen; nitric acid; sodium acetate; N,N,N',N'-tetramethyl-1,8-diaminonaphthalene; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine; sodium bis(2-methoxyethoxy)aluminium dihydride; platinum(IV) oxide; In tetrahydrofuran; nitromethane; ethanol; toluene;

DOI:10.1021/jm00398a017

Reference yield:

4-benzyloxy-2-nitro-chlorobenzene (79035-13-5) → (5-Benzyloxy-1-hydroxymethyl-8-methyl-1,6-dihydro-2H-pyrrolo[3,2-e]indol-3-yl)-(5-methoxy-1H-indol-2-yl)-methanone (101134-49-0)

Guidance literature:

Multi-step reaction with 11 steps

1: 77 percent / NaH / dimethylsulfoxide / 24 h / 105 - 115 °C

2: 40 percent / diisobutylaluminum hydride / tetrahydrofuran / 2.3 h / Ambient temperature

3: 69 percent / hydrogen / 84.5percent PtO₂ / ethanol / 2.75 h / 2327.2 Torr

4: 111 g / pyridine / 1.42 h / 5 °C

5: 1.) sodium acetate, 2.) triethylamine / 1.) ethanol, reflux, 20 h, 2.) methylene chloride

6: 64 percent / nitric acid / nitromethane / 0.67 h / 0 °C

7: 81 percent / hydrogen / 84.5percent PtO₂ / tetrahydrofuran; ethanol / 2 h / 2068.6 Torr

8: 1.) sulfuryl chloride, 2.) 1,8-bis(dimethylamino)naphthalene / 1.) methylene chloride, -70 deg C, 45 min, 2.) -70 deg C, 4 h

9: 90 percent / borane-methyl sulfide, 4-Angstroem molecular sieves / tetrahydrofuran / 3 h / Heating

10: sodium bis(2-methoxyethoxy)aluminum hydride / tetrahydrofuran; toluene

11: 1-ethyl-3-<3-(dimethylamino)propyl>carbodiimide hydrochloride

With pyridine; sulfuryl dichloride; dimethylsulfide borane complex; 4 A molecular sieve; hydrogen; nitric acid; sodium acetate; N,N,N',N'-tetramethyl-1,8-diaminonaphthalene; sodium hydride; diisobutylaluminium hydride; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine; sodium bis(2-methoxyethoxy)aluminium dihydride; platinum(IV) oxide; In tetrahydrofuran; nitromethane; ethanol; dimethyl sulfoxide; toluene;

DOI:10.1021/jm00398a017

upstream raw materials:

5-methoxy-1H-indole-2-carboxylic acid

5-(benzyloxy)-1,2,3,6-tetrahydro-8-methylbenzo<1,2-b:4,3-b'>dipyrrole-1-methanol

3-nitro-4-chlorophenol

2-[4-(benzyloxy)-2-nitrophenyl]propane-1,3-diol

Downstream raw materials:

C₂₂H₁₉N₃O₃

Methanesulfonic acid 5-benzyloxy-3-(5-methoxy-1H-indole-2-carbonyl)-8-methyl-1,2,3,6-tetrahydro-pyrrolo[3,2-e]indol-1-ylmethyl ester

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