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
• Article Data: 5

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

General Description

2-Methyl-8-(pyridin-2-yl)benzofuro[2,3-b]pyridine is a chemical compound with the molecular formula C18H13N3. It is a heterocyclic chemical, meaning it contains atoms of at least two different elements in its rings. Its structure includes a benzofuro[2,3-b]pyridine core with a pyridin-2-yl group and a methyl group attached. The specific properties, uses, and safety information regarding this compound aren't widely documented in existing literature, which implies it's likely used in specific, specialized research contexts. Handling and usage of such chemicals should always be carried out by professionals or under professional guidance, taking into consideration proper safety precautions.

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

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

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