1H-Pyrrolo[2,3-c]pyridine-3-acetic acid, 4-Methoxy-7-(3-Methyl-1H-1,2,4-triazol-1-yl)-α-oxo-, Methyl ester

Base Information

• Chemical Name: 1H-Pyrrolo[2,3-c]pyridine-3-acetic acid, 4-Methoxy-7-(3-Methyl-1H-1,2,4-triazol-1-yl)-α-oxo-, Methyl ester
• CAS No.: 701214-00-8
• Molecular Formula: C14H13N5O4
• Molecular Weight: 315.288
• Mol file: 701214-00-8.mol

Synonyms:1H-Pyrrolo[2,3-c]pyridine-3-acetic acid, 4-Methoxy-7-(3-Methyl-1H-1,2,4-triazol-1-yl)-Alpha-oxo-, Methyl ester-11;1H-Pyrrolo[2,3-c]pyridine-3-acetic acid, 4-methoxy-7-(3-methyl-1H-1,2,4-triazol-1-yl)-Alpha-oxo-,methyl ester;

Chemical Property of 1H-Pyrrolo[2,3-c]pyridine-3-acetic acid, 4-Methoxy-7-(3-Methyl-1H-1,2,4-triazol-1-yl)-α-oxo-, Methyl ester

Chemical Property:

• Boiling Point: 610.9±65.0 °C(Predicted)
• PKA: 10.58±0.40(Predicted)
• PSA: 111.99000
• Density: 1.52±0.1 g/cm3(Predicted)
• LogP: 0.81630

Purity/Quality:

97% ^*data from raw suppliers

Methyl2-(4-methoxy-7-(3-methyl-1H-1,2,4-triazol-1-yl)-1H-pyrrolo[2,3-c]pyridin-3-yl)-2-oxoacetate 95%+ ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of 1H-Pyrrolo[2,3-c]pyridine-3-acetic acid, 4-Methoxy-7-(3-Methyl-1H-1,2,4-triazol-1-yl)-α-oxo-, Methyl ester

There total 2 articles about 1H-Pyrrolo[2,3-c]pyridine-3-acetic acid, 4-Methoxy-7-(3-Methyl-1H-1,2,4-triazol-1-yl)-α-oxo-, Methyl ester 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:

2-amino-5-bromo-4-methylpyridine (98198-48-2) → methyl 2-(4-methoxy-7-(3-methyl-1H-1,2,4-triazol-1-yl)-1H-pyrrolo[2,3-c]pyridin-3-yl)-2-oxoacetate (701214-00-8)

Guidance literature:

Multi-step reaction with 9 steps

1.1: sulfuric acid; nitric acid / water / 7 h / 25 - 33 °C / Large scale

2.1: tert.-butylnitrite; sulfuric acid / 9.5 h / 20 - 43 °C / Large scale

3.1: N,N-dimethyl-formamide / 80 - 100 °C / Large scale

4.1: methanol; propanoic acid methyl ester; copper(l) iodide / tetrahydrofuran / 21 h / 30 - 72 °C / Large scale

5.1: 5%-palladium/activated carbon; hydrogen / ethyl acetate / 24 h / 25 - 35 °C / 1275.13 - 1500.15 Torr / Autoclave; Large scale

5.2: 10 - 30 °C / Large scale

6.1: trichlorophosphate / neat (no solvent) / 15 h / 40 - 102 °C / Large scale

7.1: methanol / toluene / 8 h / 45 - 55 °C / Large scale

8.1: Methyl isobutyl carbinol / 76 h / 130 - 145 °C / Large scale

9.1: isopropylmagnesium chloride; pyridine / 2-methyltetrahydrofuran / -25 - -10 °C / Large scale

9.2: 3 h / -25 - -10 °C / Large scale

With pyridine; methanol; Methyl isobutyl carbinol; copper(l) iodide; tert.-butylnitrite; propanoic acid methyl ester; sulfuric acid; 5%-palladium/activated carbon; hydrogen; isopropylmagnesium chloride; nitric acid; trichlorophosphate; In tetrahydrofuran; 2-methyltetrahydrofuran; water; ethyl acetate; N,N-dimethyl-formamide; toluene; 2.1: |Sandmeyer Reaction / 3.1: |Leimgruber-Batcho Indole Synthesis / 5.1: |Leimgruber-Batcho Indole Synthesis;

DOI:10.1021/acs.oprd.7b00134

Reference yield:

5-bromo-2-chloro-3-nitropyridine (67443-38-3) → methyl 2-(4-methoxy-7-(3-methyl-1H-1,2,4-triazol-1-yl)-1H-pyrrolo[2,3-c]pyridin-3-yl)-2-oxoacetate (701214-00-8)

Guidance literature:

Multi-step reaction with 4 steps

1: tetrahydrofuran / 1.5 h / -78 °C / Inert atmosphere

2: copper(l) iodide / methanol / 110 °C / Microwave irradiation; Inert atmosphere

3: 20 h / 143 °C / Inert atmosphere

4: aluminum (III) chloride / dichloromethane / 20 °C

With aluminum (III) chloride; copper(l) iodide; In tetrahydrofuran; methanol; dichloromethane;

DOI:10.1016/j.bmcl.2014.10.027

Reference yield: 82.6%

methyl 2-(4-methoxy-7-(3-methyl-1H-1,2,4-triazol-1-yl)-1H-pyrrolo[2,3-c]pyridin-3-yl)-2-oxoacetate (701214-00-8) + N-benzoylpiperazine hydrochloride (56227-55-5,79332-89-1) → 1-(4-benzoylpiperazin-1-yl)-2-(4-methoxy-7-(3-methyl-1H-1,2,4-triazol-1-yl)-1H-pyrrolo[2,3-c]pyridin-3-yl)-ethane-1,2-dione (701213-36-7)

Guidance literature:

With sodium t-butanolate; In tetrahydrofuran; N,N-dimethyl-formamide; at 17 - 20 ℃; for 1h;

upstream raw materials:

5-bromo-2-chloro-3-nitropyridine

2-amino-5-bromo-4-methylpyridine

Downstream raw materials:

1-(4-benzoylpiperazin-1-yl)-2-(4-methoxy-7-(3-methyl-1H-1,2,4-triazol-1-yl)-1H-pyrrolo[2,3-c]pyridin-3-yl)-ethane-1,2-dione

1,3-dihydroxy-2-(hydroxymethyl)propan-2-aminium (3-(2-(4-benzoylpiperazin-1-yl)-2-oxoacetyl)-4-methoxy-7-(3-methyl-1H-1,2,4-triazol-1-yl)-1H-pyrrolo[2,3-c]pyridin-1-yl)methyl hydrogen phosphate

C₂₅H₂₄ClN₇O₄

C₂₁H₁₈ClN₅O₄S