3-chloro-2-[7-fluoro-4-(6-methylpyrimidin-4-ylamino)pyrazolo[4,3-c]pyridin-2-yl]-5-formylbenzonitrile

Base Information

• Chemical Name: 3-chloro-2-[7-fluoro-4-(6-methylpyrimidin-4-ylamino)pyrazolo[4,3-c]pyridin-2-yl]-5-formylbenzonitrile
• CAS No.: 1378040-89-1
• Molecular Formula: C₁₉H₁₁ClFN₇O
• Molecular Weight: 407.794
• Mol file: 1378040-89-1.mol

Synonyms:3-chloro-2-[7-fluoro-4-(6-methylpyrimidin-4-ylamino)pyrazolo[4,3-c]pyridin-2-yl]-5-formylbenzonitrile

Chemical Property of 3-chloro-2-[7-fluoro-4-(6-methylpyrimidin-4-ylamino)pyrazolo[4,3-c]pyridin-2-yl]-5-formylbenzonitrile

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 3-chloro-2-[7-fluoro-4-(6-methylpyrimidin-4-ylamino)pyrazolo[4,3-c]pyridin-2-yl]-5-formylbenzonitrile

There total 9 articles about 3-chloro-2-[7-fluoro-4-(6-methylpyrimidin-4-ylamino)pyrazolo[4,3-c]pyridin-2-yl]-5-formylbenzonitrile 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: 60.0%

3-chloro-2-[7-fluoro-4-(6-methylpyrimidin-4-ylamino)pyrazolo[4,3-c]pyridin-2-yl]-5-vinylbenzonitrile (1378040-88-0) → 3-chloro-2-[7-fluoro-4-(6-methylpyrimidin-4-ylamino)pyrazolo[4,3-c]pyridin-2-yl]-5-formylbenzonitrile (1378040-89-1)

Guidance literature:

With sodium periodate; osmium(VIII) oxide; In water; acetone; at 20 ℃;

Reference yield:

4-chloro-3-fluoro-pyridine (2546-56-7) → 3-chloro-2-[7-fluoro-4-(6-methylpyrimidin-4-ylamino)pyrazolo[4,3-c]pyridin-2-yl]-5-formylbenzonitrile (1378040-89-1)

Guidance literature:

Multi-step reaction with 9 steps

1.1: diisopropylamine; n-butyllithium / hexane; tetrahydrofuran / 18.75 h / -78 - -30 °C

1.2: 20 °C

2.1: sodium azide / N,N-dimethyl-formamide / 18 h / 20 °C

3.1: triethylamine; titanium tetrachloride / dichloromethane / 2 h / 0 - 20 °C / Inert atmosphere

4.1: toluene / 5 h / Reflux

5.1: dihydrogen peroxide; methyltrioxorhenium(VII) / dichloromethane / 20 °C

6.1: triethylamine / 1,1'-bis(diphenylphosphino)ferrocenedichloropalladium (II) chloroform / propan-1-ol / 1.5 h / 100 °C

7.1: phosphorus(V) oxybromide / dichloromethane / 3 h / 0 °C

8.1: caesium carbonate / 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene; tris-(dibenzylideneacetone)dipalladium⁽⁰⁾ / 1,4-dioxane / 80 °C / Inert atmosphere; Sealed tube

9.1: osmium(VIII) oxide; sodium periodate / water; acetone / 20 °C

With sodium periodate; osmium(VIII) oxide; n-butyllithium; sodium azide; dihydrogen peroxide; titanium tetrachloride; methyltrioxorhenium(VII); caesium carbonate; triethylamine; diisopropylamine; phosphorus(V) oxybromide; tris-(dibenzylideneacetone)dipalladium⁽⁰⁾; 1,1'-bis(diphenylphosphino)ferrocenedichloropalladium (II) chloroform; 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene; In tetrahydrofuran; 1,4-dioxane; propan-1-ol; hexane; dichloromethane; water; N,N-dimethyl-formamide; acetone; toluene;

Reference yield:

4-chloro-5-fluoropyridine-3-carboxaldehyde (1060802-34-7) → 3-chloro-2-[7-fluoro-4-(6-methylpyrimidin-4-ylamino)pyrazolo[4,3-c]pyridin-2-yl]-5-formylbenzonitrile (1378040-89-1)

Guidance literature:

Multi-step reaction with 8 steps

1: sodium azide / N,N-dimethyl-formamide / 18 h / 20 °C

2: triethylamine; titanium tetrachloride / dichloromethane / 2 h / 0 - 20 °C / Inert atmosphere

3: toluene / 5 h / Reflux

4: dihydrogen peroxide; methyltrioxorhenium(VII) / dichloromethane / 20 °C

5: triethylamine / 1,1'-bis(diphenylphosphino)ferrocenedichloropalladium (II) chloroform / propan-1-ol / 1.5 h / 100 °C

6: phosphorus(V) oxybromide / dichloromethane / 3 h / 0 °C

7: caesium carbonate / 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene; tris-(dibenzylideneacetone)dipalladium⁽⁰⁾ / 1,4-dioxane / 80 °C / Inert atmosphere; Sealed tube

8: osmium(VIII) oxide; sodium periodate / water; acetone / 20 °C

With sodium periodate; osmium(VIII) oxide; sodium azide; dihydrogen peroxide; titanium tetrachloride; methyltrioxorhenium(VII); caesium carbonate; triethylamine; phosphorus(V) oxybromide; tris-(dibenzylideneacetone)dipalladium⁽⁰⁾; 1,1'-bis(diphenylphosphino)ferrocenedichloropalladium (II) chloroform; 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene; In 1,4-dioxane; propan-1-ol; dichloromethane; water; N,N-dimethyl-formamide; acetone; toluene;

upstream raw materials:

4-chloro-3-fluoro-pyridine

4-chloro-5-fluoropyridine-3-carboxaldehyde

4-azido-5-fluoro-pyridine-3-carbaldehyde

2-{[1-(4-azido-5-fluoropyridin-3-yl)meth-(E)-ylidene]amino}-5-bromo-3-chloro benzonitrile

Downstream raw materials:

3-chloro-2-[7-fluoro-4-(6-methylpyrimidin-4-ylamino)pyrazolo[4,3-c]pyridin-2-yl]-5-hydroxymethyl benzonitrile