tert-butyl 3-chloro-4-(4-chlorothiazolo[5,4-c]pyridin-2-yl)-5-fluorophenylcarbamate

Base Information

• Chemical Name: tert-butyl 3-chloro-4-(4-chlorothiazolo[5,4-c]pyridin-2-yl)-5-fluorophenylcarbamate
• CAS No.: 1365993-15-2
• Molecular Formula: C₁₇H₁₄Cl₂FN₃O₂S
• Molecular Weight: 414.287
• Mol file: 1365993-15-2.mol

Synonyms:tert-butyl 3-chloro-4-(4-chlorothiazolo[5,4-c]pyridin-2-yl)-5-fluorophenylcarbamate

Chemical Property of tert-butyl 3-chloro-4-(4-chlorothiazolo[5,4-c]pyridin-2-yl)-5-fluorophenylcarbamate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of tert-butyl 3-chloro-4-(4-chlorothiazolo[5,4-c]pyridin-2-yl)-5-fluorophenylcarbamate

There total 13 articles about tert-butyl 3-chloro-4-(4-chlorothiazolo[5,4-c]pyridin-2-yl)-5-fluorophenylcarbamate 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: 78.9%

tert-butyl carbazate (4248-19-5) + 4-chloro-2-(2-chloro-6-fluoro-4-iodophenyl)thiazolo[5,4-c]pyridine (1365993-14-1) → tert-butyl 3-chloro-4-(4-chlorothiazolo[5,4-c]pyridin-2-yl)-5-fluorophenylcarbamate (1365993-15-2)

Guidance literature:

With potassium phosphate; tris-(dibenzylideneacetone)dipalladium⁽⁰⁾; 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene; In toluene; at 90 ℃; for 20h; Inert atmosphere;

Reference yield:

2-chloro-3-fluoro-pyridine-4-carboxylic acid (628691-93-0) → tert-butyl 3-chloro-4-(4-chlorothiazolo[5,4-c]pyridin-2-yl)-5-fluorophenylcarbamate (1365993-15-2)

Guidance literature:

Multi-step reaction with 5 steps

1.1: diphenyl phosphoryl azide / toluene / 3 h / 110 °C / Inert atmosphere

2.1: trifluoroacetic acid / dichloromethane / 5 h / 20 °C

2.2: NH₂ cartridge

3.1: lithium hexamethyldisilazane / tetrahydrofuran / 0 - 20 °C

3.2: -78 °C

4.1: thionyl chloride / 120 h / 90 °C

4.2: 4 h / 85 °C

4.3: 4 h / 85 °C

5.1: potassium phosphate / 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene; tris-(dibenzylideneacetone)dipalladium⁽⁰⁾ / toluene / 20 h / 90 °C / Inert atmosphere

With potassium phosphate; thionyl chloride; diphenyl phosphoryl azide; trifluoroacetic acid; lithium hexamethyldisilazane; tris-(dibenzylideneacetone)dipalladium⁽⁰⁾; 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene; In tetrahydrofuran; dichloromethane; toluene;

Reference yield:

dimethyl 2-chloro-6-fluoroterephthalate (1258298-25-7) → tert-butyl 3-chloro-4-(4-chlorothiazolo[5,4-c]pyridin-2-yl)-5-fluorophenylcarbamate (1365993-15-2)

Guidance literature:

Multi-step reaction with 9 steps

1.1: sodium hydroxide / N,N-dimethyl-formamide / 0.5 h / 20 °C

1.2: pH 3

2.1: triethylamine; diphenyl phosphoryl azide / 20 h / 85 °C

3.1: trifluoroacetic acid / dichloromethane / 4 h / 20 °C

3.2: pH 10

4.1: hydrogenchloride; sodium nitrite / water / 0 °C

4.2: 0 - 20 °C

5.1: pyridine; lithium iodide / 4 h / 115 °C

5.2: pH 4

6.1: thionyl chloride / 2 h / 80 °C

7.1: lithium hexamethyldisilazane / tetrahydrofuran / 0 - 20 °C

7.2: -78 °C

8.1: thionyl chloride / 120 h / 90 °C

8.2: 4 h / 85 °C

8.3: 4 h / 85 °C

9.1: potassium phosphate / 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene; tris-(dibenzylideneacetone)dipalladium⁽⁰⁾ / toluene / 20 h / 90 °C / Inert atmosphere

With pyridine; hydrogenchloride; potassium phosphate; thionyl chloride; diphenyl phosphoryl azide; triethylamine; trifluoroacetic acid; sodium hydroxide; lithium iodide; lithium hexamethyldisilazane; sodium nitrite; tris-(dibenzylideneacetone)dipalladium⁽⁰⁾; 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene; In tetrahydrofuran; dichloromethane; water; N,N-dimethyl-formamide; toluene;

upstream raw materials:

2-chloro-3-fluoro-pyridine-4-carboxylic acid

tert-butyl carbazate

4-chloro-2-(2-chloro-6-fluoro-4-iodophenyl)thiazolo[5,4-c]pyridine

dimethyl 2-chloro-6-fluoroterephthalate

Downstream raw materials:

2-(4-amino-2-chloro-6-fluorophenyl)-N-(6-methylpyrimidin-4-yl)thiazolo[5,4-c]pyridin-4-amine

Refernces