1609373-99-0

Basic information

• Product Name: 2-Methyl-8-(pyridin-2-yl)benzofuro[2,3-b]pyridine
• Synonyms: 2-Methyl-8-(pyridin-2-yl)benzofuro[2,3-b]pyridine;2-methyl-8-(pyridin-2-yl)bnzofuro[2,3-b]pyridine;BZF-Pd
• CAS NO: 1609373-99-0
• Molecular Formula: C₁₇H₁₂N₂O
• Molecular Weight: 260.28998
• Mol File: 1609373-99-0.mol

Chemical Properties

• Boiling Point: 444.0±40.0 °C(Predicted)
• Appearance: /
• Density: 1.248±0.06 g/cm3(Predicted)
• Storage Temp.: Inert atmosphere,Room Temperature
• PKA: 3.83±0.40(Predicted)
• CAS DataBase Reference: 2-Methyl-8-(pyridin-2-yl)benzofuro[2,3-b]pyridine(CAS DataBase Reference)
• NIST Chemistry Reference: 2-Methyl-8-(pyridin-2-yl)benzofuro[2,3-b]pyridine(1609373-99-0)
• EPA Substance Registry System: 2-Methyl-8-(pyridin-2-yl)benzofuro[2,3-b]pyridine(1609373-99-0)

Safety Data

• Hazardous Substances Data: 1609373-99-0(Hazardous Substances Data)

Usage

Uses

Given the limited information available on 2-Methyl-8-(pyridin-2-yl)benzofuro[2,3-b]pyridine, its uses are primarily speculative and would be determined by its chemical properties and potential reactivity. However, based on its structure, it could potentially be used in the following applications:
Used in Pharmaceutical Research:
2-Methyl-8-(pyridin-2-yl)benzofuro[2,3-b]pyridine could be used as a research compound for the development of new drugs, particularly in the area of heterocyclic chemistry, where its unique structure might offer novel interactions with biological targets.
Used in Chemical Synthesis:
In the field of organic synthesis, this compound might serve as an intermediate or a building block in the synthesis of more complex molecules, especially those with potential applications in materials science or as specialty chemicals.
Used in Academic Research:
2-Methyl-8-(pyridin-2-yl)benzofuro[2,3-b]pyridine could be employed in academic research to study its physical and chemical properties, such as its reactivity, stability, and potential interactions with other molecules, which could lead to new insights in chemistry.

Synthetic route

2-bromo-pyridine (109-04-6) + 2-methyl-8-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzofuro[2,3-b]pyridine (1609374-04-0) → 1,2-methyl-8-(2-pyridine)benzofuran[2,3-B]pyridine (1609373-99-0)

Conditions	Yield
Stage #1: 2-bromo-pyridine; 2-methyl-8-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzofuro[2,3-b]pyridine With potassium carbonate In tetrahydrofuran for 0.5h; Inert atmosphere; Stage #2: With tetrakis(triphenylphosphine) palladium(0) at 80℃; for 12h;	80%

2-methylbenzofuran[2,3-b]pyridin-8-yl-trifluoromethanesulfonate (1609373-98-9) + pyridin-2-ylzinc(II) bromide → 1,2-methyl-8-(2-pyridine)benzofuran[2,3-B]pyridine (1609373-99-0)

Conditions	Yield
With tris-(dibenzylideneacetone)dipalladium(0); XPhos In tetrahydrofuran at 60 - 65℃; for 12h;	65%

(2,3-dimethoxyphenyl)boronic acid (40972-86-9) → 1,2-methyl-8-(2-pyridine)benzofuran[2,3-B]pyridine (1609373-99-0)

Conditions	Yield
Multi-step reaction with 5 steps 1: sodium carbonate; tetrakis(triphenylphosphine) palladium(0) / 1,2-dimethoxyethane; water / 5 h / Reflux 2: acetic acid; tert.-butylnitrite / tetrahydrofuran / 2 h / 0 °C 3: pyridine hydrochloride / 15 h / 200 °C 4: pyridine / dichloromethane / 0 °C 5: tris-(dibenzylideneacetone)dipalladium(0); XPhos / tetrahydrofuran / 12 h / 60 - 65 °C View Scheme

2-amino-3-bromo-6-methyl-pyridine (126325-46-0) → 1,2-methyl-8-(2-pyridine)benzofuran[2,3-B]pyridine (1609373-99-0)

Conditions	Yield
Multi-step reaction with 5 steps 1: sodium carbonate; tetrakis(triphenylphosphine) palladium(0) / 1,2-dimethoxyethane; water / 5 h / Reflux 2: acetic acid; tert.-butylnitrite / tetrahydrofuran / 2 h / 0 °C 3: pyridine hydrochloride / 15 h / 200 °C 4: pyridine / dichloromethane / 0 °C 5: tris-(dibenzylideneacetone)dipalladium(0); XPhos / tetrahydrofuran / 12 h / 60 - 65 °C View Scheme

3-(2,3-dimethoxyphenyl)-6-methylpyridin-2-amine (1609373-95-6) → 1,2-methyl-8-(2-pyridine)benzofuran[2,3-B]pyridine (1609373-99-0)

Conditions	Yield
Multi-step reaction with 4 steps 1: acetic acid; tert.-butylnitrite / tetrahydrofuran / 2 h / 0 °C 2: pyridine hydrochloride / 15 h / 200 °C 3: pyridine / dichloromethane / 0 °C 4: tris-(dibenzylideneacetone)dipalladium(0); XPhos / tetrahydrofuran / 12 h / 60 - 65 °C View Scheme

8-methoxy-2-methylbenzofuro[2,3-b]pyridine (1609373-96-7) → 1,2-methyl-8-(2-pyridine)benzofuran[2,3-B]pyridine (1609373-99-0)

Conditions	Yield
Multi-step reaction with 3 steps 1: pyridine hydrochloride / 15 h / 200 °C 2: pyridine / dichloromethane / 0 °C 3: tris-(dibenzylideneacetone)dipalladium(0); XPhos / tetrahydrofuran / 12 h / 60 - 65 °C View Scheme
Multi-step reaction with 3 steps 1: pyridine hydrochloride / 200 °C 2: dichloromethane / 0 - 20 °C 3: magnesium / tetrahydrofuran / 35 - 45 °C View Scheme

2-methylbenzofuro[2,3-b]pyridine-8-ol (1609373-97-8) → 1,2-methyl-8-(2-pyridine)benzofuran[2,3-B]pyridine (1609373-99-0)

Conditions	Yield
Multi-step reaction with 2 steps 1: pyridine / dichloromethane / 0 °C 2: tris-(dibenzylideneacetone)dipalladium(0); XPhos / tetrahydrofuran / 12 h / 60 - 65 °C View Scheme

2-methylbenzofuran[2,3-b]pyridin-8-yl-trifluoromethanesulfonate (1609373-98-9) → 1,2-methyl-8-(2-pyridine)benzofuran[2,3-B]pyridine (1609373-99-0)

Conditions	Yield
Multi-step reaction with 2 steps 1.1: potassium acetate; (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; 1,1'-bis-(diphenylphosphino)ferrocene / 1,4-dioxane / 80 °C 2.1: potassium carbonate / tetrahydrofuran / 0.5 h / Inert atmosphere 2.2: 12 h / 80 °C View Scheme

2-bromo-pyridine (109-04-6) + 2-methylbenzofuran[2,3-b]pyridin-8-yl-trifluoromethanesulfonate (1609373-98-9) → 1,2-methyl-8-(2-pyridine)benzofuran[2,3-B]pyridine (1609373-99-0)

Conditions	Yield
With magnesium In tetrahydrofuran at 35 - 45℃;

2-Amino-6-methylpyridine (1824-81-3) → 1,2-methyl-8-(2-pyridine)benzofuran[2,3-B]pyridine (1609373-99-0)

Conditions

Yield

Multi-step reaction with 7 steps 1: N-chloro-succinimide; bromine / tetrahydrofuran / 25 - 30 °C 2: toluene; ethanol; water / Reflux 3: acetic acid; tert.-butylnitrite / tetrahydrofuran / -20 °C 4: hydrogen; sodium carbonate; palladium on activated charcoal / tetrahydrofuran / 20 - 60 °C 5: pyridine hydrochloride / 200 °C 6: dichloromethane / 0 - 20 °C 7: magnesium / tetrahydrofuran / 35 - 45 °C View Scheme

3-bromo-5-chloro-6-methylpyridin-2-amine → 1,2-methyl-8-(2-pyridine)benzofuran[2,3-B]pyridine (1609373-99-0)

Conditions	Yield
Multi-step reaction with 6 steps 1: toluene; ethanol; water / Reflux 2: acetic acid; tert.-butylnitrite / tetrahydrofuran / -20 °C 3: hydrogen; sodium carbonate; palladium on activated charcoal / tetrahydrofuran / 20 - 60 °C 4: pyridine hydrochloride / 200 °C 5: dichloromethane / 0 - 20 °C 6: magnesium / tetrahydrofuran / 35 - 45 °C View Scheme

C14H15ClN2O2 → 1,2-methyl-8-(2-pyridine)benzofuran[2,3-B]pyridine (1609373-99-0)

Conditions	Yield
Multi-step reaction with 5 steps 1: acetic acid; tert.-butylnitrite / tetrahydrofuran / -20 °C 2: hydrogen; sodium carbonate; palladium on activated charcoal / tetrahydrofuran / 20 - 60 °C 3: pyridine hydrochloride / 200 °C 4: dichloromethane / 0 - 20 °C 5: magnesium / tetrahydrofuran / 35 - 45 °C View Scheme

C13H10ClNO2 → 1,2-methyl-8-(2-pyridine)benzofuran[2,3-B]pyridine (1609373-99-0)

Conditions	Yield
Multi-step reaction with 4 steps 1: hydrogen; sodium carbonate; palladium on activated charcoal / tetrahydrofuran / 20 - 60 °C 2: pyridine hydrochloride / 200 °C 3: dichloromethane / 0 - 20 °C 4: magnesium / tetrahydrofuran / 35 - 45 °C View Scheme

1,2-methyl-8-(2-pyridine)benzofuran[2,3-B]pyridine (1609373-99-0) → 2-d3-methyl-8-(pyridin-2-yl)benzofuro[2,3-b]pyridine (1609374-00-6)

Conditions	Yield
With sodium ethanolate In ethyl [2]alcohol for 72h; Reflux;	80%
With dimethylsulfoxide-d6; sodium t-butanolate at 80℃; for 12h;	80%

1,2-methyl-8-(2-pyridine)benzofuran[2,3-B]pyridine (1609373-99-0) + C28H40IrN2O2(1+)*CF3O3S(1-) → C43H43IrN4O

Conditions	Yield
In 2-ethoxy-ethanol; N,N-dimethyl-formamide at 130℃; for 18h;	61%

1,2-methyl-8-(2-pyridine)benzofuran[2,3-B]pyridine (1609373-99-0) + C26H36IrN2O2(1+)*CF3O3S(1-) → C41H39IrN4O

Conditions	Yield
In 2-ethoxy-ethanol; N,N-dimethyl-formamide at 130℃; for 18h;	60%

1,2-methyl-8-(2-pyridine)benzofuran[2,3-B]pyridine (1609373-99-0) + C24H32IrN2O2(1+)*CF3O3S(1-) → C39H35IrN4O

Conditions	Yield
In 2-ethoxy-ethanol; N,N-dimethyl-formamide at 130℃; for 18h;	58%

1,2-methyl-8-(2-pyridine)benzofuran[2,3-B]pyridine (1609373-99-0) + C24H26IrN2O2(1+)*CF3O3S(1-) (1215692-14-0, 1532554-40-7) → C39H30IrN4O (1609368-30-0)

Conditions	Yield
In ethanol for 20h; Reflux;	46%

1,2-methyl-8-(2-pyridine)benzofuran[2,3-B]pyridine (1609373-99-0) → C39H27(2)H3IrN4O (1609368-31-1)

Conditions	Yield
Multi-step reaction with 2 steps 1: sodium ethanolate / ethyl [2]alcohol / 72 h / Reflux 2: 2-ethoxy-ethanol; N,N-dimethyl-formamide / 18 h / 130 °C View Scheme

1,2-methyl-8-(2-pyridine)benzofuran[2,3-B]pyridine (1609373-99-0) → C41H25(2)H9IrN4O (1609368-32-2)

Conditions	Yield
Multi-step reaction with 2 steps 1: sodium ethanolate / ethyl [2]alcohol / 72 h / Reflux 2: 2-ethoxy-ethanol; N,N-dimethyl-formamide / 18 h / 130 °C / Inert atmosphere View Scheme

1,2-methyl-8-(2-pyridine)benzofuran[2,3-B]pyridine (1609373-99-0) → C41H30(2)H9IrN4O

Conditions	Yield
Multi-step reaction with 2 steps 1: sodium t-butanolate; dimethylsulfoxide-d6 / 12 h / 80 °C 2: 2-ethoxy-ethanol; N,N-dimethyl-formamide / 18 h / 130 °C View Scheme

1,2-methyl-8-(2-pyridine)benzofuran[2,3-B]pyridine (1609373-99-0) → C43H28(2)H15IrN4O

Conditions	Yield
Multi-step reaction with 2 steps 1: sodium t-butanolate; dimethylsulfoxide-d6 / 12 h / 80 °C 2: 2-ethoxy-ethanol; N,N-dimethyl-formamide / 18 h / 130 °C View Scheme

iridium(III) chloride monohydrate + 1,2-methyl-8-(2-pyridine)benzofuran[2,3-B]pyridine (1609373-99-0) → (1,2-methyl-8-(2-pyridine)benzofuran[2,3-B]pyridine)4Ir2Cl2

Conditions	Yield
In 2-ethoxy-ethanol; water

Upstream product

• 40972-86-9 (2,3-dimethoxyphenyl)boronic acid 
• 126325-46-0 2-amino-3-bromo-6-methyl-pyridine 
• 1609373-95-6 3-(2,3-dimethoxyphenyl)-6-methylpyridin-2-amine 
• 1609373-96-7 8-methoxy-2-methylbenzofuro[2,3-b]pyridine 
• 1609373-97-8 2-methylbenzofuro[2,3-b]pyridine-8-ol 
• 1609373-98-9 2-methylbenzofuran[2,3-b]pyridin-8-yl-trifluoromethanesulfonate 
• 109-04-6 2-bromo-pyridine 
• 1609374-04-0 2-methyl-8-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzofuro[2,3-b]pyridine 
• 1824-81-3 2-Amino-6-methylpyridine 
• 952948-94-6 3-bromo-5-chloro-6-methylpyridin-2-amine 

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