tert-butyl 6-amino-1-methyl-7-(2-(3-bromophenyl)ethynyl)-1H-imidazo[4,5-d]pyridin-4-yl(methyl)carbamate

Base Information

• Chemical Name: tert-butyl 6-amino-1-methyl-7-(2-(3-bromophenyl)ethynyl)-1H-imidazo[4,5-d]pyridin-4-yl(methyl)carbamate
• CAS No.: 914943-95-6
• Molecular Formula: C₂₁H₂₂BrN₅O₂
• Molecular Weight: 456.342
• Mol file: 914943-95-6.mol

Synonyms:tert-butyl 6-amino-1-methyl-7-(2-(3-bromophenyl)ethynyl)-1H-imidazo[4,5-d]pyridin-4-yl(methyl)carbamate

Chemical Property of tert-butyl 6-amino-1-methyl-7-(2-(3-bromophenyl)ethynyl)-1H-imidazo[4,5-d]pyridin-4-yl(methyl)carbamate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of tert-butyl 6-amino-1-methyl-7-(2-(3-bromophenyl)ethynyl)-1H-imidazo[4,5-d]pyridin-4-yl(methyl)carbamate

There total 17 articles about tert-butyl 6-amino-1-methyl-7-(2-(3-bromophenyl)ethynyl)-1H-imidazo[4,5-d]pyridin-4-yl(methyl)carbamate 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: 100.0%

tert-butyl (6-amino-7-iodo-1-methyl-1H-imidazo[4,5-c]pyridin-4-yl)(methyl)carbamate (914942-88-4) + 3-bromophenylacetylene (766-81-4) → tert-butyl 6-amino-1-methyl-7-(2-(3-bromophenyl)ethynyl)-1H-imidazo[4,5-d]pyridin-4-yl(methyl)carbamate (914943-95-6)

Guidance literature:

With copper(l) iodide; triethylamine; bis-triphenylphosphine-palladium(II) chloride; In N,N-dimethyl-formamide; at 75 ℃; for 0.5h;

Reference yield:

2,6-dichloro-N-methylpyridine-4-amine (175461-33-3) → tert-butyl 6-amino-1-methyl-7-(2-(3-bromophenyl)ethynyl)-1H-imidazo[4,5-d]pyridin-4-yl(methyl)carbamate (914943-95-6)

Guidance literature:

Multi-step reaction with 10 steps

1.1: sulfuric acid / 1.5 h / -5 - 0 °C

1.2: 2 h / 0 °C

2.1: sulfuric acid / 2 h / 0 °C

3.1: ammonium chloride / iron / water / 2 h / 20 - 90 °C

4.1: ethanol / 15 h / 20 - 80 °C

5.1: ethanol / 3 - 24 h / 82 - 120 °C

6.1: sodium hexamethyldisilazane / tetrahydrofuran / 0.58 - 1 h / -78 - -20 °C

6.2: 3.5 - 16 h / -20 - 20 °C

7.1: caesium carbonate; 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene / tris-(dibenzylideneacetone)dipalladium⁽⁰⁾ / N,N-dimethyl acetamide / 5 - 8.33 h / 110 - 115 °C

8.1: hydrogenchloride / tetrahydrofuran; water / 0.33 - 0.5 h / 0 - 5 °C

8.2: pH 12

9.1: N-iodo-succinimide / acetonitrile / 2.25 h / 0 °C / Cooling with ethanol-dry ice

10.1: copper(l) iodide; triethylamine / bis-triphenylphosphine-palladium(II) chloride / N,N-dimethyl-formamide / 0.5 h / 75 °C

With hydrogenchloride; N-iodo-succinimide; copper(l) iodide; sulfuric acid; sodium hexamethyldisilazane; ammonium chloride; caesium carbonate; triethylamine; 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene; bis-triphenylphosphine-palladium(II) chloride; tris-(dibenzylideneacetone)dipalladium⁽⁰⁾; iron; In tetrahydrofuran; ethanol; N,N-dimethyl acetamide; water; N,N-dimethyl-formamide; acetonitrile;

Reference yield:

2,4,6-trichloropyridine (16063-69-7) → tert-butyl 6-amino-1-methyl-7-(2-(3-bromophenyl)ethynyl)-1H-imidazo[4,5-d]pyridin-4-yl(methyl)carbamate (914943-95-6)

Guidance literature:

Multi-step reaction with 10 steps

1.1: ethanol / 1.66 - 24 h / 20 - 60 °C

2.1: sulfuric acid; nitric acid / 0.92 h / 0 - 6 °C

3.1: ammonium chloride / iron / water / 2 h / 20 - 90 °C

4.1: ethanol / 15 h / 20 - 80 °C

5.1: ethanol / 3 - 24 h / 82 - 120 °C

6.1: sodium hexamethyldisilazane / tetrahydrofuran / 0.58 - 1 h / -78 - -20 °C

6.2: 3.5 - 16 h / -20 - 20 °C

7.1: caesium carbonate; 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene / tris-(dibenzylideneacetone)dipalladium⁽⁰⁾ / N,N-dimethyl acetamide / 5 - 8.33 h / 110 - 115 °C

8.1: hydrogenchloride / tetrahydrofuran; water / 0.33 - 0.5 h / 0 - 5 °C

8.2: pH 12

9.1: N-iodo-succinimide / acetonitrile / 2.25 h / 0 °C / Cooling with ethanol-dry ice

10.1: copper(l) iodide; triethylamine / bis-triphenylphosphine-palladium(II) chloride / N,N-dimethyl-formamide / 0.5 h / 75 °C

With hydrogenchloride; N-iodo-succinimide; copper(l) iodide; sulfuric acid; nitric acid; sodium hexamethyldisilazane; ammonium chloride; caesium carbonate; triethylamine; 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene; bis-triphenylphosphine-palladium(II) chloride; tris-(dibenzylideneacetone)dipalladium⁽⁰⁾; iron; In tetrahydrofuran; ethanol; N,N-dimethyl acetamide; water; N,N-dimethyl-formamide; acetonitrile;

upstream raw materials:

tert-butyl (6-amino-7-iodo-1-methyl-1H-imidazo[4,5-c]pyridin-4-yl)(methyl)carbamate

3-bromophenylacetylene

pyridin-4-ol

2,4,6-trichloropyridine

Downstream raw materials:

7-(3-bromophenyl)-1,6-dihydro-N,1-dimethyl-1-(tert-butyloxycarbonyl)-imidazo[4,5-d]pyrrolo[2,3-b]pyridin-4-amine

Refernces