4-methoxy-7-(3-methyl-1H-1,2,4-triazol-1-yl)-1H-pyrrolo[2,3-c]pyridine

Base Information

• Chemical Name: 4-methoxy-7-(3-methyl-1H-1,2,4-triazol-1-yl)-1H-pyrrolo[2,3-c]pyridine
• CAS No.: 676491-46-6
• Molecular Formula: C11H11N5O
• Molecular Weight: 229.241
• Hs Code.: 2933990090
• DSSTox Substance ID: DTXSID70580925
• Wikidata: Q82471927
• Mol file: 676491-46-6.mol

Synonyms:676491-46-6;4-methoxy-7-(3-methyl-1H-1,2,4-triazol-1-yl)-1H-pyrrolo[2,3-c]pyridine;1H-Pyrrolo[2,3-c]pyridine, 4-methoxy-7-(3-methyl-1H-1,2,4-triazol-1-yl)-;4-Methoxy-7-(3-methyl-1,2,4-triazol-1-yl)-1H-pyrrolo[2,3-c]pyridine;1-{4-methoxy-1H-pyrrolo[2,3-c]pyridin-7-yl}-3-methyl-1H-1,2,4-triazole;MFCD19105151;SCHEMBL1475279;DTXSID70580925;BCB49146;AKOS025291120;AS-72923;SY098256;CS-0006832;A867221;J-515654;4-Methoxy-7-(3-methyl-1H-1,2,4-triazol-1-yl)-6-azaindole

Chemical Property of 4-methoxy-7-(3-methyl-1H-1,2,4-triazol-1-yl)-1H-pyrrolo[2,3-c]pyridine

Chemical Property:

• Boiling Point: 525.2±60.0 °C(Predicted)
• PKA: 13.04±0.40(Predicted)
• PSA: 68.62000
• Density: 1.44±0.1 g/cm3(Predicted)
• LogP: 1.46060
• XLogP3: 1.4
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 2
• Exact Mass: 229.09635999
• Heavy Atom Count: 17
• Complexity: 277

Purity/Quality:

97% ^*data from raw suppliers

4-Methoxy-7-(3-methyl-1h-1,2,4-triazol-1-yl)-1h-pyrrolo[2,3-C]pyridine ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC1=NN(C=N1)C2=NC=C(C3=C2NC=C3)OC

Technology Process of 4-methoxy-7-(3-methyl-1H-1,2,4-triazol-1-yl)-1H-pyrrolo[2,3-c]pyridine

There total 2 articles about 4-methoxy-7-(3-methyl-1H-1,2,4-triazol-1-yl)-1H-pyrrolo[2,3-c]pyridine 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) → 4-methoxy-7-(3-methyl-1H-1,2,4-triazol-1-yl)-1H-pyrrolo[2,3-c]pyridine (676491-46-6) + 4-methoxy-7-(5-methyl-1H-1,2,4-triazol-1-yl)-1H-pyrrolo[2,3-c]pyridine (701213-99-2) + C11H11N5O

Guidance literature:

Multi-step reaction with 8 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

With methanol; Methyl isobutyl carbinol; copper(l) iodide; tert.-butylnitrite; propanoic acid methyl ester; sulfuric acid; 5%-palladium/activated carbon; hydrogen; nitric acid; trichlorophosphate; In tetrahydrofuran; 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) → 4-methoxy-7-(3-methyl-1H-1,2,4-triazol-1-yl)-1H-pyrrolo[2,3-c]pyridine (676491-46-6)

Guidance literature:

Multi-step reaction with 3 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

With copper(l) iodide; In tetrahydrofuran; methanol;

DOI:10.1016/j.bmcl.2014.10.027

Reference yield:

4-methoxy-7-(3-methyl-1H-1,2,4-triazol-1-yl)-1H-pyrrolo[2,3-c]pyridine (676491-46-6) → (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 di-tert-butyl phosphate

Guidance literature:

Multi-step reaction with 6 steps

1.1: isopropylmagnesium chloride / tetrahydrofuran

2.1: N,N,N',N'-tetramethylguanidine / 1-methyl-pyrrolidin-2-one / 2 h / 20 °C / Industry scale; Inert atmosphere

2.2: 18.03 h / 20 °C / Industry scale

3.1: tetrabutoxytitanium / 2-methyltetrahydrofuran / 3 h / Inert atmosphere; Reflux

4.1: chlorine / dichloromethane / -3 - 3 °C / Inert atmosphere; Industry scale

5.1: dichloromethane; water / 20 - 25 °C / Industry scale; Inert atmosphere

6.1: potassium di-tert-butylphosphate; tetraethylammonium bromide / dichloromethane / 1 h / 33 - 42 °C / Inert atmosphere; Industry scale

With tetrabutoxytitanium; tetraethylammonium bromide; isopropylmagnesium chloride; chlorine; potassium di-tert-butylphosphate; N,N,N',N'-tetramethylguanidine; In tetrahydrofuran; 2-methyltetrahydrofuran; 1-methyl-pyrrolidin-2-one; dichloromethane; water;

upstream raw materials:

5-bromo-2-chloro-3-nitropyridine

2-amino-5-bromo-4-methylpyridine

Downstream raw materials:

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

C₃₁H₂₈ClN₇O₄S