(R)-3-(3-fluorophenyl)-N-(1-hydroxy-3-(1H-indol-3-yl)propan-2-yl)-8-methoxy-9-(morpholine-4-carbonyl)-5,6-dihydropyrrolo[2,1-a]isoquinoline-2-carboxamide

Base Information

• Chemical Name: (R)-3-(3-fluorophenyl)-N-(1-hydroxy-3-(1H-indol-3-yl)propan-2-yl)-8-methoxy-9-(morpholine-4-carbonyl)-5,6-dihydropyrrolo[2,1-a]isoquinoline-2-carboxamide
• CAS No.: 1428796-12-6
• Molecular Formula: C₃₆H₃₅FN₄O₅
• Molecular Weight: 622.696
• Mol file: 1428796-12-6.mol

Synonyms:(R)-3-(3-fluorophenyl)-N-(1-hydroxy-3-(1H-indol-3-yl)propan-2-yl)-8-methoxy-9-(morpholine-4-carbonyl)-5,6-dihydropyrrolo[2,1-a]isoquinoline-2-carboxamide

Chemical Property of (R)-3-(3-fluorophenyl)-N-(1-hydroxy-3-(1H-indol-3-yl)propan-2-yl)-8-methoxy-9-(morpholine-4-carbonyl)-5,6-dihydropyrrolo[2,1-a]isoquinoline-2-carboxamide

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (R)-3-(3-fluorophenyl)-N-(1-hydroxy-3-(1H-indol-3-yl)propan-2-yl)-8-methoxy-9-(morpholine-4-carbonyl)-5,6-dihydropyrrolo[2,1-a]isoquinoline-2-carboxamide

There total 12 articles about (R)-3-(3-fluorophenyl)-N-(1-hydroxy-3-(1H-indol-3-yl)propan-2-yl)-8-methoxy-9-(morpholine-4-carbonyl)-5,6-dihydropyrrolo[2,1-a]isoquinoline-2-carboxamide 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:

4-amino-3-methoxybenzaldehyde (90151-40-9) → (R)-3-(3-fluorophenyl)-N-(1-hydroxy-3-(1H-indol-3-yl)propan-2-yl)-8-methoxy-9-(morpholine-4-carbonyl)-5,6-dihydropyrrolo[2,1-a]isoquinoline-2-carboxamide (1428796-12-6)

Guidance literature:

Multi-step reaction with 10 steps

1: n-Butyl nitrite; copper(I) bromide / acetonitrile / 18 h / 20 °C

2: ammonium acetate; acetic acid / 18 h / 80 °C

3: sodium tetrahydroborate; borane-THF / tetrahydrofuran / 18 h / 0 - 65 °C / Inert atmosphere

4: N-ethyl-N,N-diisopropylamine / dichloromethane / 1 h / 0 - 20 °C / Inert atmosphere

5: trichlorophosphate / toluene / 2 h / 110 °C

6: potassium carbonate; triethylamine / acetonitrile / 2 h / 100 °C

7: palladium diacetate; sodium carbonate; 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene / toluene / 80 °C

8: palladium diacetate; caesium carbonate; triphenylphosphine / 1,4-dioxane / 21.25 h / 80 °C / Inert atmosphere; Sealed tube

9: water; sodium hydroxide / ethanol / 18 h / 50 °C

10: benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine / N,N-dimethyl-formamide / 70 h / 20 °C

With sodium tetrahydroborate; borane-THF; n-Butyl nitrite; ammonium acetate; water; palladium diacetate; sodium carbonate; potassium carbonate; benzotriazol-1-ol; caesium carbonate; acetic acid; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine; N-ethyl-N,N-diisopropylamine; triphenylphosphine; 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene; copper(I) bromide; sodium hydroxide; trichlorophosphate; In tetrahydrofuran; 1,4-dioxane; ethanol; dichloromethane; N,N-dimethyl-formamide; toluene; acetonitrile;

Reference yield:

3-(3-fluorophenyl)-8-methoxy-9-(morpholine-4-carbonyl)-5,6-dihydropyrrolo[2,1-a]isoquinoline-2-carboxylic acid (1428796-85-3) + (2R)-2-amino-3-(1H-indol-3-yl)propan-1-ol (154-09-6,526-53-4,2899-29-8,52485-52-6) → (R)-3-(3-fluorophenyl)-N-(1-hydroxy-3-(1H-indol-3-yl)propan-2-yl)-8-methoxy-9-(morpholine-4-carbonyl)-5,6-dihydropyrrolo[2,1-a]isoquinoline-2-carboxamide (1428796-12-6)

Guidance literature:

With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine; In N,N-dimethyl-formamide; at 20 ℃; for 70h;

Reference yield:

3-methoxy-4-nitrobenzaldehyde (80410-57-7) → (R)-3-(3-fluorophenyl)-N-(1-hydroxy-3-(1H-indol-3-yl)propan-2-yl)-8-methoxy-9-(morpholine-4-carbonyl)-5,6-dihydropyrrolo[2,1-a]isoquinoline-2-carboxamide (1428796-12-6)

Guidance literature:

Multi-step reaction with 11 steps

1: iron; ammonium chloride / ethanol; water / 2 h / 78 °C

2: n-Butyl nitrite; copper(I) bromide / acetonitrile / 18 h / 20 °C

3: ammonium acetate; acetic acid / 18 h / 80 °C

4: sodium tetrahydroborate; borane-THF / tetrahydrofuran / 18 h / 0 - 65 °C / Inert atmosphere

5: N-ethyl-N,N-diisopropylamine / dichloromethane / 1 h / 0 - 20 °C / Inert atmosphere

6: trichlorophosphate / toluene / 2 h / 110 °C

7: potassium carbonate; triethylamine / acetonitrile / 2 h / 100 °C

8: palladium diacetate; sodium carbonate; 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene / toluene / 80 °C

9: palladium diacetate; caesium carbonate; triphenylphosphine / 1,4-dioxane / 21.25 h / 80 °C / Inert atmosphere; Sealed tube

10: water; sodium hydroxide / ethanol / 18 h / 50 °C

11: benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine / N,N-dimethyl-formamide / 70 h / 20 °C

With sodium tetrahydroborate; borane-THF; n-Butyl nitrite; ammonium acetate; water; palladium diacetate; iron; sodium carbonate; potassium carbonate; ammonium chloride; benzotriazol-1-ol; caesium carbonate; acetic acid; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine; N-ethyl-N,N-diisopropylamine; triphenylphosphine; 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene; copper(I) bromide; sodium hydroxide; trichlorophosphate; In tetrahydrofuran; 1,4-dioxane; ethanol; dichloromethane; water; N,N-dimethyl-formamide; toluene; acetonitrile;

upstream raw materials:

3-methoxy-4-nitrobenzaldehyde

5-formyl-2-nitrophenol

4-amino-3-methoxybenzaldehyde

4-bromo-3-methoxybenzaldehyde

Refernces