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24958-42-7

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24958-42-7 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.

Check Digit Verification of cas no

The CAS Registry Mumber 24958-42-7 includes 8 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 5 digits, 2,4,9,5 and 8 respectively; the second part has 2 digits, 4 and 2 respectively.
Calculate Digit Verification of CAS Registry Number 24958-42:
(7*2)+(6*4)+(5*9)+(4*5)+(3*8)+(2*4)+(1*2)=137
137 % 10 = 7
So 24958-42-7 is a valid CAS Registry Number.
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)

24958-42-7SDS

SAFETY DATA SHEETS

According to Globally Harmonized System of Classification and Labelling of Chemicals (GHS) - Sixth revised edition

Version: 1.0

Creation Date: Aug 11, 2017

Revision Date: Aug 11, 2017

1.Identification

1.1 GHS Product identifier

Product name 2-bromo-4-methoxy-5-phenylmethoxybenzoic acid

1.2 Other means of identification

Product number -
Other names 2-Bromo-4-methoxy-5-benzyloxybenzoic acid

1.3 Recommended use of the chemical and restrictions on use

Identified uses For industry use only.
Uses advised against no data available

1.4 Supplier's details

1.5 Emergency phone number

Emergency phone number -
Service hours Monday to Friday, 9am-5pm (Standard time zone: UTC/GMT +8 hours).

More Details:24958-42-7 SDS

24958-42-7Synthetic route

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

5-benzyloxy-2-bromo-4-methoxybenzaldehyde

2-bromo-4-methoxy-5-benzyloxy-benzoic acid
24958-42-7

2-bromo-4-methoxy-5-benzyloxy-benzoic acid

Conditions
ConditionsYield
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-bromo-4-methoxy-5-benzyloxy-benzoic acid

[2-(4-benzyloxy-phenyl)-ethyl]methylamine
38961-21-6

[2-(4-benzyloxy-phenyl)-ethyl]methylamine

5-benzyloxy-N-[2-(4-benzyloxy-phenyl)-ethyl]-2-bromo-4-methoxy-N-methylbenzamide
24958-43-8

5-benzyloxy-N-[2-(4-benzyloxy-phenyl)-ethyl]-2-bromo-4-methoxy-N-methylbenzamide

Conditions
ConditionsYield
With phenylboronic acid In toluene at 110℃; for 30h;93%
2-bromo-4-methoxy-5-benzyloxy-benzoic acid
24958-42-7

2-bromo-4-methoxy-5-benzyloxy-benzoic acid

recorcinol
108-46-3

recorcinol

8-(benzyloxy)-3-hydroxy-9-methoxy-6H-benzo[c]chromen-6-one

8-(benzyloxy)-3-hydroxy-9-methoxy-6H-benzo[c]chromen-6-one

Conditions
ConditionsYield
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

2-bromo-4-methoxy-5-benzyloxy-benzoic acid

5-Benzyloxy-2-bromo-4-methoxybenzoylchlorid
27240-64-8

5-Benzyloxy-2-bromo-4-methoxybenzoylchlorid

Conditions
ConditionsYield
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

2-bromo-4-methoxy-5-benzyloxy-benzoic acid

N-[(diphenylphosphinyl)methyl]-N-[(4-methoxyphenyl)methyl]-5-(benzyloxy)-2-bromo-4-methoxybenzamide
206002-18-8

N-[(diphenylphosphinyl)methyl]-N-[(4-methoxyphenyl)methyl]-5-(benzyloxy)-2-bromo-4-methoxybenzamide

Conditions
ConditionsYield
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

2-bromo-4-methoxy-5-benzyloxy-benzoic acid

6-benzyloxy-5-methoxy-2-(4-methoxy-benzyl)-2,3-dihydro-isoindol-1-one

6-benzyloxy-5-methoxy-2-(4-methoxy-benzyl)-2,3-dihydro-isoindol-1-one

Conditions
ConditionsYield
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

2-bromo-4-methoxy-5-benzyloxy-benzoic acid

6-(benzyloxy)-3-[(2-bromo-6-methoxyphenyl)methylene]-2,3-dihydro-5-methoxy-2-[(4-methoxyphenyl)methyl]-1H-isoindol-1-one

6-(benzyloxy)-3-[(2-bromo-6-methoxyphenyl)methylene]-2,3-dihydro-5-methoxy-2-[(4-methoxyphenyl)methyl]-1H-isoindol-1-one

Conditions
ConditionsYield
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

2-bromo-4-methoxy-5-benzyloxy-benzoic acid

benzotriazol-1-ol
2592-95-2

benzotriazol-1-ol

5-benzyloxy-2-bromo-4-methoxy benzoic acid benzotriazole-1-yl ester
873195-14-3

5-benzyloxy-2-bromo-4-methoxy benzoic acid benzotriazole-1-yl ester

Conditions
ConditionsYield
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

3-methoxycarbonylindole

2-bromo-4-methoxy-5-benzyloxy-benzoic acid
24958-42-7

2-bromo-4-methoxy-5-benzyloxy-benzoic acid

5-(benzyloxy)-4-methoxy-2-[3-(methoxycarbonyl)-1H-indol-1-yl]benzoic acid

5-(benzyloxy)-4-methoxy-2-[3-(methoxycarbonyl)-1H-indol-1-yl]benzoic acid

Conditions
ConditionsYield
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

2-bromo-4-methoxy-5-benzyloxy-benzoic acid

N-[4-(benzyloxy)phenyl]-N-phenyl-1H-indole-3-carboxamide

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

5-(benzyloxy)-2-(3-{[4-(benzyloxy)phenyl](phenyl)carbamoyl}-1H-indol-1-yl)-4-methoxybenzoic acid

Conditions
ConditionsYield
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

2-bromo-4-methoxy-5-benzyloxy-benzoic acid

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

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
ConditionsYield
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

2-bromo-4-methoxy-5-benzyloxy-benzoic acid

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

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
ConditionsYield
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

2-bromo-4-methoxy-5-benzyloxy-benzoic acid

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

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
ConditionsYield
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

2-bromo-4-methoxy-5-benzyloxy-benzoic acid

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

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
ConditionsYield
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

2-bromo-4-methoxy-5-benzyloxy-benzoic acid

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

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
ConditionsYield
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

2-bromo-4-methoxy-5-benzyloxy-benzoic acid

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

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
ConditionsYield
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

2-bromo-4-methoxy-5-benzyloxy-benzoic acid

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

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
ConditionsYield
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

2-bromo-4-methoxy-5-benzyloxy-benzoic acid

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

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
ConditionsYield
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

2-bromo-4-methoxy-5-benzyloxy-benzoic acid

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

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
ConditionsYield
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

2-bromo-4-methoxy-5-benzyloxy-benzoic acid

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

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
ConditionsYield
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

2-bromo-4-methoxy-5-benzyloxy-benzoic acid

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

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
ConditionsYield
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

24958-42-7Relevant articles and documents

Alternative total synthesis of (-)-galanthamine hydrobromide

Reddy, Jambula Mukunda,Kumar, Kotagiri Vijay,Raju, Veeramalla,Bhaskar, Bolguddu Vijay,Himabindu, Vurumidi,Bhattacharya, Apurba,Sundaram, Venkatram,Banerjee, Rahul,Reddy, Ghanta Mahesh,Bandichhor, Rakeshwar

, p. 2138 - 2149 (2008/09/21)

An alternative total synthesis of (-)-galanthamine (1) hydrobromide, employing ecofriendly amidation, oxidative coupling, and classical resolution strategies is accomplished. Copyright Taylor & Francis Group, LLC.

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