3-[1,6-dihydro-1-methyl-4-((methyl)tert-butoxycarbonylamino)imidazo[4,5-d]pyrrolo[2,3-b]pyridin-7-yl]-5-fluoro-benzoic acid methyl ester

Base Information

• Chemical Name: 3-[1,6-dihydro-1-methyl-4-((methyl)tert-butoxycarbonylamino)imidazo[4,5-d]pyrrolo[2,3-b]pyridin-7-yl]-5-fluoro-benzoic acid methyl ester
• CAS No.: 914944-27-7
• Molecular Formula: C₂₃H₂₄FN₅O₄
• Molecular Weight: 453.473
• Mol file: 914944-27-7.mol

Synonyms:3-[1,6-dihydro-1-methyl-4-((methyl)tert-butoxycarbonylamino)imidazo[4,5-d]pyrrolo[2,3-b]pyridin-7-yl]-5-fluoro-benzoic acid methyl ester

Chemical Property of 3-[1,6-dihydro-1-methyl-4-((methyl)tert-butoxycarbonylamino)imidazo[4,5-d]pyrrolo[2,3-b]pyridin-7-yl]-5-fluoro-benzoic acid methyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 3-[1,6-dihydro-1-methyl-4-((methyl)tert-butoxycarbonylamino)imidazo[4,5-d]pyrrolo[2,3-b]pyridin-7-yl]-5-fluoro-benzoic acid methyl ester

There total 23 articles about 3-[1,6-dihydro-1-methyl-4-((methyl)tert-butoxycarbonylamino)imidazo[4,5-d]pyrrolo[2,3-b]pyridin-7-yl]-5-fluoro-benzoic acid methyl ester 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: 87.0%

3-((4-tert-butyloxycarbonyl(methyl)amino)-1-methyl-6-(2,2,2-trifluoroacetamido)-1H-imidazo[4,5-c]pyridin-7-yl)ethynyl-5-fluorobenzoic acid methyl ester (914944-26-6) → 3-[1,6-dihydro-1-methyl-4-((methyl)tert-butoxycarbonylamino)imidazo[4,5-d]pyrrolo[2,3-b]pyridin-7-yl]-5-fluoro-benzoic acid methyl ester (914944-27-7)

Guidance literature:

With potassium carbonate; tetrakis(triphenylphosphine) palladium⁽⁰⁾; In N,N-dimethyl acetamide; at 130 ℃; for 0.75h; Microwave irradiation;

Reference yield:

2,4,6-trichloropyridine (16063-69-7) → 3-[1,6-dihydro-1-methyl-4-((methyl)tert-butoxycarbonylamino)imidazo[4,5-d]pyrrolo[2,3-b]pyridin-7-yl]-5-fluoro-benzoic acid methyl ester (914944-27-7)

Guidance literature:

Multi-step reaction with 12 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: triethylamine / bis-triphenylphosphine-palladium(II) chloride / 0.5 h / 90 °C

11.1: triethylamine / dichloromethane / 0.33 h / 0 - 20 °C

12.1: potassium carbonate / tetrakis(triphenylphosphine) palladium⁽⁰⁾ / N,N-dimethyl acetamide / 0.75 h / 130 °C / Microwave irradiation

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

Reference yield:

2,6-dichloro-N-methylpyridine-4-amine (175461-33-3) → 3-[1,6-dihydro-1-methyl-4-((methyl)tert-butoxycarbonylamino)imidazo[4,5-d]pyrrolo[2,3-b]pyridin-7-yl]-5-fluoro-benzoic acid methyl ester (914944-27-7)

Guidance literature:

Multi-step reaction with 11 steps

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

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

3.1: ethanol / 15 h / 20 - 80 °C

4.1: ethanol / 3 - 24 h / 82 - 120 °C

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

5.2: 3.5 - 16 h / -20 - 20 °C

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

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

7.2: pH 12

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

9.1: triethylamine / bis-triphenylphosphine-palladium(II) chloride / 0.5 h / 90 °C

10.1: triethylamine / dichloromethane / 0.33 h / 0 - 20 °C

11.1: potassium carbonate / tetrakis(triphenylphosphine) palladium⁽⁰⁾ / N,N-dimethyl acetamide / 0.75 h / 130 °C / Microwave irradiation

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

upstream raw materials:

3-((4-tert-butyloxycarbonyl(methyl)amino)-1-methyl-6-(2,2,2-trifluoroacetamido)-1H-imidazo[4,5-c]pyridin-7-yl)ethynyl-5-fluorobenzoic acid methyl ester

3-bromo-5-fluorobenzoic acid

methyl 3-bromo-5-fluoro-benzoate

pyridin-4-ol

Downstream raw materials:

3-[1,6-dihydro-1-methyl-4-((methyl)tert-butoxycarbonylamino)imidazo[4,5-d]pyrrolo[2,3-b]pyridin-7-yl]-5-fluoro-benzoic acid