24958-42-7

Basic information

• Product Name: 2-Bromo-4-methoxy-5-benzyloxybenzoic acid
• Synonyms: 3-BROMO-4-METHOXY-5-BENZYLOXYBENZOIC ACID;5-BENZYLOXY-2-BROMO-4-METHOXY-BENZOIC ACID;2-BROMO-5-BENZYLOXY-4-METHOXYBENZOIC ACID;2-BROMO-4-METHOXY-5-(BENZYLOXY)BENZOIC ACID;2-BROMO-4-METHOXY-5-(PHENYLMETHOXY)BENZOIC ACID;5-Benzyloxy-2-Bromo-4-Methoxyb;2-brono-5-benzyloxy-4-methoxybenzoic acid;5-Benzyl-2-bromo-4-methoxylbenzoic acid
• CAS NO: 24958-42-7
• Molecular Formula: C₁₅H₁₃BrO₄
• Molecular Weight: 337.17
• Product Categories: Multisubstituted Benzene;Aromatic Carboxylic Acids, Amides, Anilides, Anhydrides & Salts;API intermediates
• Mol File: 24958-42-7.mol
• Article Data: 2

Chemical Properties

• Melting Point: 193.0 to 197.0 °C
• Boiling Point: 445.442 ºC at 760 mmHg
• Flash Point: 223.196 ºC
• Appearance: /
• Density: 1.486 g/cm³
• Vapor Pressure: 0mmHg at 25°C
• Refractive Index: 1.611
• Storage Temp.: 2-8°C
• PKA: 2.97±0.10(Predicted)
• CAS DataBase Reference: 2-Bromo-4-methoxy-5-benzyloxybenzoic acid(CAS DataBase Reference)
• NIST Chemistry Reference: 2-Bromo-4-methoxy-5-benzyloxybenzoic acid(24958-42-7)
• EPA Substance Registry System: 2-Bromo-4-methoxy-5-benzyloxybenzoic acid(24958-42-7)

Safety Data

• Hazardous Substances Data: 24958-42-7(Hazardous Substances Data)

Usage

Description

2-Bromo-4-methoxy-5-benzyloxybenzoic acid is an organic compound that serves as a crucial intermediate in the synthesis of various pharmaceutical and cosmetic agents. It is characterized by its bromine atom at the 2nd position, methoxy and benzyloxy groups at the 4th and 5th positions, respectively, and a carboxylic acid functional group. 2-Bromo-4-methoxy-5-benzyloxybenzoic acid is known for its potential applications in the development of anti-aging and anti-wrinkle products, as well as its ability to promote collagen production and inhibit certain enzymes.

Uses

Used in Pharmaceutical Industry:
2-Bromo-4-methoxy-5-benzyloxybenzoic acid is used as an intermediate in the synthesis of 3,8-Dihydroxy-9-methoxy-6H-Dibenzo[b,d]pyran-6-one (D455545), a compound with potential applications in the development of anti-wrinkle agents. It is known for its ability to promote collagen production, which is essential for maintaining skin elasticity and firmness.
Used in Cosmetic Industry:
In the cosmetic industry, 2-Bromo-4-methoxy-5-benzyloxybenzoic acid is used as a key component in the formulation of anti-aging and anti-wrinkle products. It is known to inhibit the production of MMP-1, an enzyme that degrades collagen and contributes to the formation of wrinkles. Additionally, it acts as an elastase activity inhibitor, which helps maintain the skin's elasticity and prevents sagging.
Used in Research and Development:
2-Bromo-4-methoxy-5-benzyloxybenzoic acid is also utilized in research and development for the discovery and development of new pharmaceutical and cosmetic agents. Its unique chemical structure and functional groups make it a valuable compound for exploring novel applications and potential synergistic effects with other compounds in various formulations.

InChI:InChI=1/C15H13BrO4/c1-19-13-8-12(16)11(15(17)18)7-14(13)20-9-10-5-3-2-4-6-10/h2-8H,9H2,1H3,(H,17,18)

Synthetic route

5-benzyloxy-2-bromo-4-methoxybenzaldehyde (6451-86-1) → 2-bromo-4-methoxy-5-benzyloxy-benzoic acid (24958-42-7)

Conditions	Yield
With potassium permanganate In methanol; water at 50 - 55℃;	70%
Stage #1: 5-benzyloxy-2-bromo-4-methoxybenzaldehyde With hydrogenchloride; potassium permanganate In acetone Stage #2: With potassium hydroxide In acetone

2-bromo-4-methoxy-5-benzyloxy-benzoic acid (24958-42-7) + [2-(4-benzyloxy-phenyl)-ethyl]methylamine (38961-21-6) → 5-benzyloxy-N-[2-(4-benzyloxy-phenyl)-ethyl]-2-bromo-4-methoxy-N-methylbenzamide (24958-43-8)

Conditions	Yield
With phenylboronic acid In toluene at 110℃; for 30h;	93%

2-bromo-4-methoxy-5-benzyloxy-benzoic acid (24958-42-7) + recorcinol (108-46-3) → 8-(benzyloxy)-3-hydroxy-9-methoxy-6H-benzo[c]chromen-6-one

Conditions	Yield
Stage #1: 2-bromo-4-methoxy-5-benzyloxy-benzoic acid; recorcinol With sodium hydroxide In water at 120℃; for 0.75h; Stage #2: With copper(II) sulfate In water for 0.25h; Reflux;	52%

2-bromo-4-methoxy-5-benzyloxy-benzoic acid (24958-42-7) → 5-Benzyloxy-2-bromo-4-methoxybenzoylchlorid (27240-64-8)

Conditions	Yield
With thionyl chloride; N,N-dimethyl-formamide at 20℃; for 12h; Chlorination;
With thionyl chloride; N,N-dimethyl-formamide In dichloromethane Substitution;
With thionyl chloride In chloroform for 3h; Heating / reflux;
With thionyl chloride; N,N-dimethyl-formamide In dichloromethane at 30 - 35℃; for 0.5h;
With thionyl chloride; N,N-dimethyl-formamide In toluene at 68℃; for 2h;

2-bromo-4-methoxy-5-benzyloxy-benzoic acid (24958-42-7) → N-[(diphenylphosphinyl)methyl]-N-[(4-methoxyphenyl)methyl]-5-(benzyloxy)-2-bromo-4-methoxybenzamide (206002-18-8)

Conditions	Yield
Multi-step reaction with 2 steps 1: SOCl2; DMF / CH2Cl2 View Scheme
Multi-step reaction with 2 steps 1: thionyl chloride; dimethylformamide / 12 h / 20 °C 2: Et3N / CH2Cl2 / 2 h / 0 - 20 °C View Scheme

2-bromo-4-methoxy-5-benzyloxy-benzoic acid (24958-42-7) → 6-benzyloxy-5-methoxy-2-(4-methoxy-benzyl)-2,3-dihydro-isoindol-1-one

Conditions	Yield
Multi-step reaction with 3 steps 1.1: SOCl2; DMF / CH2Cl2 3.1: KHMDS / toluene; tetrahydrofuran / 2.5 h / -78 - 20 °C 3.2: 67 percent / NaOH; H2O / toluene; tetrahydrofuran / 3 h / Heating View Scheme

2-bromo-4-methoxy-5-benzyloxy-benzoic acid (24958-42-7) → 6-(benzyloxy)-3-[(2-bromo-6-methoxyphenyl)methylene]-2,3-dihydro-5-methoxy-2-[(4-methoxyphenyl)methyl]-1H-isoindol-1-one

Conditions	Yield
Multi-step reaction with 3 steps 1.1: thionyl chloride; dimethylformamide / 12 h / 20 °C 2.1: Et3N / CH2Cl2 / 2 h / 0 - 20 °C 3.1: KHMDS / toluene; tetrahydrofuran / 3.5 h / -78 - -30 °C 3.2: 81 percent / toluene; tetrahydrofuran / 0.5 h / -30 - 20 °C View Scheme

2-bromo-4-methoxy-5-benzyloxy-benzoic acid (24958-42-7) + benzotriazol-1-ol (2592-95-2) → 5-benzyloxy-2-bromo-4-methoxy benzoic acid benzotriazole-1-yl ester (873195-14-3)

Conditions	Yield
Stage #1: 2-bromo-4-methoxy-5-benzyloxy-benzoic acid; benzotriazol-1-ol In dichloromethane at 25 - 35℃; for 0.25h; Stage #2: With dicyclohexyl-carbodiimide In dichloromethane at 25 - 45℃; for 3 - 6h; Product distribution / selectivity;

3-methoxycarbonylindole (942-24-5) + 2-bromo-4-methoxy-5-benzyloxy-benzoic acid (24958-42-7) → 5-(benzyloxy)-4-methoxy-2-[3-(methoxycarbonyl)-1H-indol-1-yl]benzoic acid

Conditions	Yield
With copper(l) iodide; potassium carbonate In N,N-dimethyl-formamide at 90℃; for 16h; Inert atmosphere;
With copper(l) iodide; potassium carbonate In N,N-dimethyl-formamide at 90℃; for 16h; Inert atmosphere;

2-bromo-4-methoxy-5-benzyloxy-benzoic acid (24958-42-7) + N-[4-(benzyloxy)phenyl]-N-phenyl-1H-indole-3-carboxamide → 5-(benzyloxy)-2-(3-{[4-(benzyloxy)phenyl](phenyl)carbamoyl}-1H-indol-1-yl)-4-methoxybenzoic acid

Conditions	Yield
With copper(l) iodide; potassium carbonate In N,N-dimethyl-formamide at 80℃; for 16h; Inert atmosphere;
With copper(l) iodide; potassium carbonate In N,N-dimethyl-formamide at 80℃; for 16h; Inert atmosphere;

2-bromo-4-methoxy-5-benzyloxy-benzoic acid (24958-42-7) → 1-[4-(benzyloxy)-5-methoxy-2-[(3S)-3-[(4-methylpiperazin-1-yl)methyl]-1,2,3,4-tetrahydroisoquinoline-2-carbonyl]phenyl]-N-[4-(benzyloxy)phenyl]-N-phenyl-1H-indole-3-carboxamide

Conditions	Yield
Multi-step reaction with 2 steps 1: copper(l) iodide; potassium carbonate / N,N-dimethyl-formamide / 16 h / 80 °C / Inert atmosphere 2: N-ethyl-N,N-diisopropylamine; O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate / N,N-dimethyl-formamide / 3 h / 20 °C View Scheme

2-bromo-4-methoxy-5-benzyloxy-benzoic acid (24958-42-7) → 1-{4-hydroxy-5-methoxy-2-[(3S)-3-[(4-methylpiperazin-1-yl)methyl]-1,2,3,4-tetrahydroisoquinoline-2-carbonyl]phenyl}-N-(4-hydroxyphenyl)-N-phenyl-1H-indole-3-carboxamide

Conditions	Yield
Multi-step reaction with 3 steps 1: copper(l) iodide; potassium carbonate / N,N-dimethyl-formamide / 16 h / 80 °C / Inert atmosphere 2: N-ethyl-N,N-diisopropylamine; O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate / N,N-dimethyl-formamide / 3 h / 20 °C 3: palladium 10% on activated carbon; ammonium formate / 2.5 h / Inert atmosphere; Reflux View Scheme
Multi-step reaction with 3 steps 1: copper(l) iodide; potassium carbonate / N,N-dimethyl-formamide / 16 h / 80 °C / Inert atmosphere 2: N-ethyl-N,N-diisopropylamine; O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate / N,N-dimethyl-formamide / 3 h / 20 °C 3: palladium 10% on activated carbon; ammonium formate / methanol / 2.5 h / Inert atmosphere; Reflux View Scheme

2-bromo-4-methoxy-5-benzyloxy-benzoic acid (24958-42-7) → 1-[4-(benzyloxy)-5-methoxy-2-[(3S)-3-[(4-methylpiperazin-1-yl)methyl]-1,2,3,4-tetrahydroisoquinoline-2-carbonyl]phenyl]-1H-indole-3-carboxylic acid methyl ester

Conditions	Yield
Multi-step reaction with 2 steps 1: copper(l) iodide; potassium carbonate / N,N-dimethyl-formamide / 16 h / 90 °C / Inert atmosphere 2: N-ethyl-N,N-diisopropylamine; O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate / N,N-dimethyl-formamide / 72 h / 20 °C View Scheme
Multi-step reaction with 2 steps 1: copper(l) iodide; potassium carbonate / N,N-dimethyl-formamide / 16 h / 90 °C / Inert atmosphere 2: N-ethyl-N,N-diisopropylamine; O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate / N,N-dimethyl-formamide / 72 h / 20 °C View Scheme

2-bromo-4-methoxy-5-benzyloxy-benzoic acid (24958-42-7) → sodium 1-[4-(benzyloxy)-5-methoxy-2-[(3S)-3-[(4-methylpiperazin-1-yl)methyl]-1,2,3,4-tetrahydroisoquinoline-2-carbonyl]phenyl]-1H-indole-3-carboxylate

Conditions	Yield
Multi-step reaction with 3 steps 1: copper(l) iodide; potassium carbonate / N,N-dimethyl-formamide / 16 h / 90 °C / Inert atmosphere 2: N-ethyl-N,N-diisopropylamine; O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate / N,N-dimethyl-formamide / 72 h / 20 °C 3: methanol; sodium hydroxide / tetrahydrofuran / 7 h / 50 °C View Scheme
Multi-step reaction with 3 steps 1: copper(l) iodide; potassium carbonate / N,N-dimethyl-formamide / 16 h / 90 °C / Inert atmosphere 2: N-ethyl-N,N-diisopropylamine; O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate / N,N-dimethyl-formamide / 72 h / 20 °C 3: sodium hydroxide; water / methanol; tetrahydrofuran / 7 h / 50 °C View Scheme

2-bromo-4-methoxy-5-benzyloxy-benzoic acid (24958-42-7) → 1-[4-(benzyloxy)-5-methoxy-2-[(3S)-3-[(4-methylpiperazin-1-yl)methyl]-1,2,3,4-tetrahydroisoquinoline-2-carbonyl]phenyl]-1H-indole-3-carbonyl chloride

Conditions	Yield
Multi-step reaction with 4 steps 1: copper(l) iodide; potassium carbonate / N,N-dimethyl-formamide / 16 h / 90 °C / Inert atmosphere 2: N-ethyl-N,N-diisopropylamine; O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate / N,N-dimethyl-formamide / 72 h / 20 °C 3: methanol; sodium hydroxide / tetrahydrofuran / 7 h / 50 °C 4: oxalyl dichloride; N,N-dimethyl-formamide / dichloromethane / 16 h / 20 °C / Inert atmosphere View Scheme
Multi-step reaction with 4 steps 1: copper(l) iodide; potassium carbonate / N,N-dimethyl-formamide / 16 h / 90 °C / Inert atmosphere 2: N-ethyl-N,N-diisopropylamine; O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate / N,N-dimethyl-formamide / 72 h / 20 °C 3: sodium hydroxide; water / methanol; tetrahydrofuran / 7 h / 50 °C 4: oxalyl dichloride; N,N-dimethyl-formamide / dichloromethane / 16 h / 20 °C / Inert atmosphere View Scheme

2-bromo-4-methoxy-5-benzyloxy-benzoic acid (24958-42-7) → 1-[4-(benzyloxy)-5-methoxy-2-[(3S)-3-[(4-methylpiperazin-1-yl)methyl]-1,2,3,4-tetrahydroisoquinoline-2-carbonyl]phenyl]-N-cyclohexyl-N-phenyl-1H-indole-3-carboxamide

Conditions	Yield
Multi-step reaction with 5 steps 1: copper(l) iodide; potassium carbonate / N,N-dimethyl-formamide / 16 h / 90 °C / Inert atmosphere 2: N-ethyl-N,N-diisopropylamine; O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate / N,N-dimethyl-formamide / 72 h / 20 °C 3: methanol; sodium hydroxide / tetrahydrofuran / 7 h / 50 °C 4: oxalyl dichloride; N,N-dimethyl-formamide / dichloromethane / 16 h / 20 °C / Inert atmosphere 5: pyridine / dichloromethane / 16 h / 0 - 20 °C / Inert atmosphere View Scheme
Multi-step reaction with 5 steps 1: copper(l) iodide; potassium carbonate / N,N-dimethyl-formamide / 16 h / 90 °C / Inert atmosphere 2: N-ethyl-N,N-diisopropylamine; O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate / N,N-dimethyl-formamide / 72 h / 20 °C 3: sodium hydroxide; water / methanol; tetrahydrofuran / 7 h / 50 °C 4: oxalyl dichloride; N,N-dimethyl-formamide / dichloromethane / 16 h / 20 °C / Inert atmosphere 5: pyridine / dichloromethane / 0 - 20 °C View Scheme

2-bromo-4-methoxy-5-benzyloxy-benzoic acid (24958-42-7) → N-cyclohexyl-1-{4-hydroxy-5-methoxy-2-[(3S)-3-[(4-methylpiperazin-1-yl)-methyl]-1,2,3,4-tetrahydroisoquinoline-2-carbonyl]phenyl}-N-phenyl-1H-indole-3-carboxamide

Conditions	Yield
Multi-step reaction with 6 steps 1: copper(l) iodide; potassium carbonate / N,N-dimethyl-formamide / 16 h / 90 °C / Inert atmosphere 2: N-ethyl-N,N-diisopropylamine; O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate / N,N-dimethyl-formamide / 72 h / 20 °C 3: methanol; sodium hydroxide / tetrahydrofuran / 7 h / 50 °C 4: oxalyl dichloride; N,N-dimethyl-formamide / dichloromethane / 16 h / 20 °C / Inert atmosphere 5: pyridine / dichloromethane / 16 h / 0 - 20 °C / Inert atmosphere 6: palladium 10% on activated carbon; ammonium formate / methanol / 1 h / Inert atmosphere; Reflux View Scheme
Multi-step reaction with 6 steps 1: copper(l) iodide; potassium carbonate / N,N-dimethyl-formamide / 16 h / 90 °C / Inert atmosphere 2: N-ethyl-N,N-diisopropylamine; O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate / N,N-dimethyl-formamide / 72 h / 20 °C 3: sodium hydroxide; water / methanol; tetrahydrofuran / 7 h / 50 °C 4: oxalyl dichloride; N,N-dimethyl-formamide / dichloromethane / 16 h / 20 °C / Inert atmosphere 5: pyridine / dichloromethane / 0 - 20 °C 6: palladium 10% on activated carbon; ammonium formate / methanol / 1 h / Reflux View Scheme

2-bromo-4-methoxy-5-benzyloxy-benzoic acid (24958-42-7) → lithium 1-[4-(benzyloxy)-5-methoxy-2-[(3S)-3-[(4-methylpiperazin-1-yl)methyl]-1,2,3,4-tetrahydroisoquinoline-2-carbonyl]phenyl]-1H-indole-3-carboxylate

Conditions	Yield
Multi-step reaction with 3 steps 1: copper(l) iodide; potassium carbonate / N,N-dimethyl-formamide / 16 h / 90 °C / Inert atmosphere 2: N-ethyl-N,N-diisopropylamine; O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate / N,N-dimethyl-formamide / 72 h / 20 °C 3: lithium hydroxide / 1,4-dioxane / 32 h / Reflux View Scheme
Multi-step reaction with 3 steps 1: copper(l) iodide; potassium carbonate / N,N-dimethyl-formamide / 16 h / 90 °C / Inert atmosphere 2: N-ethyl-N,N-diisopropylamine; O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate / N,N-dimethyl-formamide / 72 h / 20 °C 3: lithium hydroxide / 1,4-dioxane / 32 h / Reflux View Scheme

2-bromo-4-methoxy-5-benzyloxy-benzoic acid (24958-42-7) → 1-[4-(benzyloxy)-5-methoxy-2-[(3S)-3-[(4-methylpiperazin-1-yl)methyl]-1,2,3,4-tetrahydroisoquinoline-2-carbonyl]phenyl]-N-{4-[(tert-butyldimethylsilyl)oxy]phenyl}-N-cyclohexyl-1H-indole-3-carboxamide

Conditions	Yield
Multi-step reaction with 4 steps 1.1: copper(l) iodide; potassium carbonate / N,N-dimethyl-formamide / 16 h / 90 °C / Inert atmosphere 2.1: N-ethyl-N,N-diisopropylamine; O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate / N,N-dimethyl-formamide / 72 h / 20 °C 3.1: lithium hydroxide / 1,4-dioxane / 32 h / Reflux 4.1: thionyl chloride / dichloromethane / 16 h / 0 - 20 °C / Inert atmosphere 4.2: 4 h / 20 °C / Inert atmosphere View Scheme
Multi-step reaction with 4 steps 1.1: copper(l) iodide; potassium carbonate / N,N-dimethyl-formamide / 16 h / 90 °C / Inert atmosphere 2.1: N-ethyl-N,N-diisopropylamine; O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate / N,N-dimethyl-formamide / 72 h / 20 °C 3.1: lithium hydroxide / 1,4-dioxane / 32 h / Reflux 4.1: thionyl chloride / dichloromethane / 18 h / 0 - 20 °C / Inert atmosphere 4.2: 4 h / 20 °C / Inert atmosphere View Scheme

2-bromo-4-methoxy-5-benzyloxy-benzoic acid (24958-42-7) → 1-[4-(benzyloxy)-5-methoxy-2-[(3S)-3-[(4-methylpiperazin-1-yl)methyl]-1,2,3,4-tetrahydroisoquinoline-2-carbonyl]phenyl]-N-cyclohexyl-N-(4-hydroxyphenyl)-1H-indole-3-carboxamide

Conditions	Yield
Multi-step reaction with 5 steps 1.1: copper(l) iodide; potassium carbonate / N,N-dimethyl-formamide / 16 h / 90 °C / Inert atmosphere 2.1: N-ethyl-N,N-diisopropylamine; O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate / N,N-dimethyl-formamide / 72 h / 20 °C 3.1: lithium hydroxide / 1,4-dioxane / 32 h / Reflux 4.1: thionyl chloride / dichloromethane / 16 h / 0 - 20 °C / Inert atmosphere 4.2: 4 h / 20 °C / Inert atmosphere 5.1: potassium hydroxide; methanol / 3 h / 20 °C View Scheme
Multi-step reaction with 5 steps 1.1: copper(l) iodide; potassium carbonate / N,N-dimethyl-formamide / 16 h / 90 °C / Inert atmosphere 2.1: N-ethyl-N,N-diisopropylamine; O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate / N,N-dimethyl-formamide / 72 h / 20 °C 3.1: lithium hydroxide / 1,4-dioxane / 32 h / Reflux 4.1: thionyl chloride / dichloromethane / 18 h / 0 - 20 °C / Inert atmosphere 4.2: 4 h / 20 °C / Inert atmosphere 5.1: water; potassium hydroxide / methanol / 3 h / 20 °C View Scheme

2-bromo-4-methoxy-5-benzyloxy-benzoic acid (24958-42-7) → N-cyclohexyl-1-{4-hydroxy-5-methoxy-2-[(3S)-3-[(4-methylpiperazin-1-yl)-methyl]-1,2,3,4-tetrahydroisoquinoline-2-carbonyl]phenyl}-N-(4-hydroxyphenyl)-1H-indole-3-carboxamide

Conditions	Yield
Multi-step reaction with 6 steps 1.1: copper(l) iodide; potassium carbonate / N,N-dimethyl-formamide / 16 h / 90 °C / Inert atmosphere 2.1: N-ethyl-N,N-diisopropylamine; O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate / N,N-dimethyl-formamide / 72 h / 20 °C 3.1: lithium hydroxide / 1,4-dioxane / 32 h / Reflux 4.1: thionyl chloride / dichloromethane / 16 h / 0 - 20 °C / Inert atmosphere 4.2: 4 h / 20 °C / Inert atmosphere 5.1: potassium hydroxide; methanol / 3 h / 20 °C 6.1: palladium 10% on activated carbon; ammonium formate / methanol / 48 h / Reflux; Inert atmosphere View Scheme
Multi-step reaction with 6 steps 1.1: copper(l) iodide; potassium carbonate / N,N-dimethyl-formamide / 16 h / 90 °C / Inert atmosphere 2.1: N-ethyl-N,N-diisopropylamine; O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate / N,N-dimethyl-formamide / 72 h / 20 °C 3.1: lithium hydroxide / 1,4-dioxane / 32 h / Reflux 4.1: thionyl chloride / dichloromethane / 18 h / 0 - 20 °C / Inert atmosphere 4.2: 4 h / 20 °C / Inert atmosphere 5.1: water; potassium hydroxide / methanol / 3 h / 20 °C 6.1: palladium 10% on activated carbon; ammonium formate / methanol / 48 h / Inert atmosphere; Reflux View Scheme

Upstream product

• 6451-86-1 5-benzyloxy-2-bromo-4-methoxybenzaldehyde 

Downstream Products

• 24958-43-8 5-benzyloxy-N-[2-(4-benzyloxy-phenyl)-ethyl]-2-bromo-4-methoxy-N-methylbenzamide 
• 206002-18-8 N-[(diphenylphosphinyl)methyl]-N-[(4-methoxyphenyl)methyl]-5-(benzyloxy)-2-bromo-4-methoxybenzamide 
• 27240-64-8 5-Benzyloxy-2-bromo-4-methoxybenzoylchlorid 

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