C₁₈H₁₆FN₃O₃

Base Information

• Chemical Name: C₁₈H₁₆FN₃O₃
• CAS No.: 1578264-57-9
• Molecular Formula: C₁₈H₁₆FN₃O₃
• Molecular Weight: 341.342
• Mol file: 1578264-57-9.mol

Synonyms:C₁₈H₁₆FN₃O₃

Chemical Property of C₁₈H₁₆FN₃O₃

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of C₁₈H₁₆FN₃O₃

There total 15 articles about C₁₈H₁₆FN₃O₃ 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:

4-hydroxy-3-nitropyridine (5435-54-1) → C18H16FN3O3 (1578264-56-8) + C18H16FN3O3 (1578264-57-9)

Guidance literature:

Multi-step reaction with 16 steps

1.1: bromine / water / 2 h / 50 °C

2.1: trichlorophosphate; diethylamine / 3 h / 0 °C

3.1: sodium hydride / N,N-dimethyl-formamide / 0.5 h / 0 °C

3.2: 1 h / 20 °C

3.3: 16 h / Reflux

4.1: N,N-dimethyl acetamide / 2 h / 90 °C

5.1: acetic acid; iron / 2 h / Reflux

6.1: triethylamine / dichloromethane / 0.17 h

6.2: 2 h / 20 °C

7.1: sodium hydroxide; copper(II) sulfate; copper bronze / water / 16 h / 160 °C

8.1: triethylamine / tetrahydrofuran; water / 2 h / 20 °C

9.1: palladium 10% on activated carbon; hydrogen / methanol / 24 h / 20 °C / 7757.43 Torr

10.1: piperidine / dichloromethane / 12 h / 20 °C

11.1: N-ethyl-N,N-diisopropylamine / dichloromethane / 12 h / 20 °C

12.1: dmap / N,N-dimethyl acetamide / 0.08 h / 20 °C / Microwave irradiation

13.1: palladium bis[bis(diphenylphosphino)ferrocene] dichloride / dimethyl amine / 1 h / 160 °C / Microwave irradiation

14.1: N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate; N-ethyl-N,N-diisopropylamine / N,N-dimethyl-formamide / 0.17 h / 0 °C

14.2: 16.33 h / 20 °C

15.1: potassium carbonate / butanone / 0.2 h / 90 °C / Microwave irradiation

16.1: CHIRAL PAK IA 250 X 50 mm, 5Mm / ethanol; hexane / 25 °C / Resolution of racemate

With piperidine; dmap; palladium bis[bis(diphenylphosphino)ferrocene] dichloride; copper bronze; palladium 10% on activated carbon; hydrogen; bromine; iron; sodium hydride; potassium carbonate; copper(II) sulfate; acetic acid; diethylamine; triethylamine; N-ethyl-N,N-diisopropylamine; N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate; sodium hydroxide; trichlorophosphate; In tetrahydrofuran; methanol; ethanol; hexane; dichloromethane; N,N-dimethyl acetamide; water; dimethyl amine; N,N-dimethyl-formamide; butanone;

DOI:10.1021/jm401625b

Reference yield:

3-bromo-5-nitropyridin-4-ol (31872-65-8) → C18H16FN3O3 (1578264-56-8) + C18H16FN3O3 (1578264-57-9)

Guidance literature:

Multi-step reaction with 15 steps

1.1: trichlorophosphate; diethylamine / 3 h / 0 °C

2.1: sodium hydride / N,N-dimethyl-formamide / 0.5 h / 0 °C

2.2: 1 h / 20 °C

2.3: 16 h / Reflux

3.1: N,N-dimethyl acetamide / 2 h / 90 °C

4.1: acetic acid; iron / 2 h / Reflux

5.1: triethylamine / dichloromethane / 0.17 h

5.2: 2 h / 20 °C

6.1: sodium hydroxide; copper(II) sulfate; copper bronze / water / 16 h / 160 °C

7.1: triethylamine / tetrahydrofuran; water / 2 h / 20 °C

8.1: palladium 10% on activated carbon; hydrogen / methanol / 24 h / 20 °C / 7757.43 Torr

9.1: piperidine / dichloromethane / 12 h / 20 °C

10.1: N-ethyl-N,N-diisopropylamine / dichloromethane / 12 h / 20 °C

11.1: dmap / N,N-dimethyl acetamide / 0.08 h / 20 °C / Microwave irradiation

12.1: palladium bis[bis(diphenylphosphino)ferrocene] dichloride / dimethyl amine / 1 h / 160 °C / Microwave irradiation

13.1: N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate; N-ethyl-N,N-diisopropylamine / N,N-dimethyl-formamide / 0.17 h / 0 °C

13.2: 16.33 h / 20 °C

14.1: potassium carbonate / butanone / 0.2 h / 90 °C / Microwave irradiation

15.1: CHIRAL PAK IA 250 X 50 mm, 5Mm / ethanol; hexane / 25 °C / Resolution of racemate

With piperidine; dmap; palladium bis[bis(diphenylphosphino)ferrocene] dichloride; copper bronze; palladium 10% on activated carbon; hydrogen; iron; sodium hydride; potassium carbonate; copper(II) sulfate; acetic acid; diethylamine; triethylamine; N-ethyl-N,N-diisopropylamine; N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate; sodium hydroxide; trichlorophosphate; In tetrahydrofuran; methanol; ethanol; hexane; dichloromethane; N,N-dimethyl acetamide; water; dimethyl amine; N,N-dimethyl-formamide; butanone;

DOI:10.1021/jm401625b

Reference yield:

3-bromo-4-chloro-5-nitropyridine (31872-63-6) → C18H16FN3O3 (1578264-56-8) + C18H16FN3O3 (1578264-57-9)

Guidance literature:

Multi-step reaction with 14 steps

1.1: sodium hydride / N,N-dimethyl-formamide / 0.5 h / 0 °C

1.2: 1 h / 20 °C

1.3: 16 h / Reflux

2.1: N,N-dimethyl acetamide / 2 h / 90 °C

3.1: acetic acid; iron / 2 h / Reflux

4.1: triethylamine / dichloromethane / 0.17 h

4.2: 2 h / 20 °C

5.1: sodium hydroxide; copper(II) sulfate; copper bronze / water / 16 h / 160 °C

6.1: triethylamine / tetrahydrofuran; water / 2 h / 20 °C

7.1: palladium 10% on activated carbon; hydrogen / methanol / 24 h / 20 °C / 7757.43 Torr

8.1: piperidine / dichloromethane / 12 h / 20 °C

9.1: N-ethyl-N,N-diisopropylamine / dichloromethane / 12 h / 20 °C

10.1: dmap / N,N-dimethyl acetamide / 0.08 h / 20 °C / Microwave irradiation

11.1: palladium bis[bis(diphenylphosphino)ferrocene] dichloride / dimethyl amine / 1 h / 160 °C / Microwave irradiation

12.1: N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate; N-ethyl-N,N-diisopropylamine / N,N-dimethyl-formamide / 0.17 h / 0 °C

12.2: 16.33 h / 20 °C

13.1: potassium carbonate / butanone / 0.2 h / 90 °C / Microwave irradiation

14.1: CHIRAL PAK IA 250 X 50 mm, 5Mm / ethanol; hexane / 25 °C / Resolution of racemate

With piperidine; dmap; palladium bis[bis(diphenylphosphino)ferrocene] dichloride; copper bronze; palladium 10% on activated carbon; hydrogen; iron; sodium hydride; potassium carbonate; copper(II) sulfate; acetic acid; triethylamine; N-ethyl-N,N-diisopropylamine; N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate; sodium hydroxide; In tetrahydrofuran; methanol; ethanol; hexane; dichloromethane; N,N-dimethyl acetamide; water; dimethyl amine; N,N-dimethyl-formamide; butanone;

DOI:10.1021/jm401625b

upstream raw materials:

4-hydroxy-3-nitropyridine

3-bromo-5-nitropyridin-4-ol

3-bromo-4-chloro-5-nitropyridine

3-bromo-4-methyl-5-nitropyridine