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

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
• CAS No.: 914944-30-2
• Molecular Formula: C₂₂H₂₂FN₅O₄
• Molecular Weight: 439.446
• Mol file: 914944-30-2.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

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

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

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 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: 80.0%

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) → 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 (914944-30-2)

Guidance literature:

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; With methanol; sodium hydroxide; water; at 100 ℃; for 0.25h; Microwave irradiation;

With hydrogenchloride; In water; pH=1 - 2;

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 (914944-30-2)

Guidance literature:

Multi-step reaction with 13 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

13.1: methanol; sodium hydroxide; water / 0.25 h / 100 °C / Microwave irradiation

13.2: pH 1 - 2

With hydrogenchloride; methanol; sodium hydroxide; N-iodo-succinimide; sulfuric acid; water; 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:

methyl 3-bromo-5-fluoro-benzoate (334792-52-8) → 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 (914944-30-2)

Guidance literature:

Multi-step reaction with 6 steps

1.1: triethylamine / bis(acetato)bis(triphenylphosphine)palladium⁽⁰⁾ / toluene

1.2: 0.5 h / 95 °C

2.1: potassium hydroxide / methanol; water / 0.5 h

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

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

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

6.1: methanol; sodium hydroxide; water / 0.25 h / 100 °C / Microwave irradiation

6.2: pH 1 - 2

With methanol; potassium hydroxide; sodium hydroxide; water; potassium carbonate; triethylamine; bis-triphenylphosphine-palladium(II) chloride; tetrakis(triphenylphosphine) palladium⁽⁰⁾; bis(acetato)bis(triphenylphosphine)palladium⁽⁰⁾; In methanol; dichloromethane; N,N-dimethyl acetamide; water; toluene;

upstream 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 methyl ester

3-bromo-5-fluorobenzoic acid

methyl 3-bromo-5-fluoro-benzoate

pyridin-4-ol

Refernces