tert-butyl methyl(1-methyl-7-phenyl-1,6-dihydroimidazo[4,5-d]pyrrolo[2,3-b]pyridin-4-yl)carbamate

Base Information

• Chemical Name: tert-butyl methyl(1-methyl-7-phenyl-1,6-dihydroimidazo[4,5-d]pyrrolo[2,3-b]pyridin-4-yl)carbamate
• CAS No.: 914942-90-8
• Molecular Formula: C₂₁H₂₃N₅O₂
• Molecular Weight: 377.446
• Mol file: 914942-90-8.mol

Synonyms:tert-butyl methyl(1-methyl-7-phenyl-1,6-dihydroimidazo[4,5-d]pyrrolo[2,3-b]pyridin-4-yl)carbamate

Chemical Property of tert-butyl methyl(1-methyl-7-phenyl-1,6-dihydroimidazo[4,5-d]pyrrolo[2,3-b]pyridin-4-yl)carbamate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of tert-butyl methyl(1-methyl-7-phenyl-1,6-dihydroimidazo[4,5-d]pyrrolo[2,3-b]pyridin-4-yl)carbamate

There total 19 articles about tert-butyl methyl(1-methyl-7-phenyl-1,6-dihydroimidazo[4,5-d]pyrrolo[2,3-b]pyridin-4-yl)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: 79.5%

tert-butyl 6-amino-1-methyl-7-(2-phenylethynyl)-1H-imidazo[4,5-c]pyridin-4-yl(methyl)carbamate (914942-89-5) → tert-butyl methyl(1-methyl-7-phenyl-1,6-dihydroimidazo[4,5-d]pyrrolo[2,3-b]pyridin-4-yl)carbamate (914942-90-8)

Guidance literature:

With potassium tert-butylate; In tetrahydrofuran; N,N-dimethyl acetamide; at 80 ℃; for 2.58333h; Product distribution / selectivity;

Reference yield: 56.0%

tert-butyl (6-amino-7-iodo-1-methyl-1H-imidazo[4,5-c]pyridin-4-yl)(methyl)carbamate (914942-88-4) + acetophenone (98-86-2) → tert-butyl methyl(1-methyl-7-phenyl-1,6-dihydroimidazo[4,5-d]pyrrolo[2,3-b]pyridin-4-yl)carbamate (914942-90-8)

Guidance literature:

acetophenone; With allyl(1,3-bis(2,6-diisopropylphenyl)imidazolidin-2-ylidene)palladium(IV) chloride; sodium hexamethyldisilazane; In tetrahydrofuran; at 20 ℃; for 0.0833333h; Inert atmosphere;

tert-butyl (6-amino-7-iodo-1-methyl-1H-imidazo[4,5-c]pyridin-4-yl)(methyl)carbamate; In tetrahydrofuran; at 20 - 100 ℃; for 4h; regioselective reaction; Inert atmosphere;

DOI:10.1021/jo100623d

Reference yield:

2,6-dichloro-N-methylpyridine-4-amine (175461-33-3) → tert-butyl methyl(1-methyl-7-phenyl-1,6-dihydroimidazo[4,5-d]pyrrolo[2,3-b]pyridin-4-yl)carbamate (914942-90-8)

Guidance literature:

Multi-step reaction with 10 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: copper(l) iodide; diisopropylamine / bis-triphenylphosphine-palladium(II) chloride / N,N-dimethyl-formamide / 0.5 h / 60 °C

10.1: 1-methyl-pyrrolidin-2-one; potassium tert-butylate / tetrahydrofuran / 2 h / 80 °C

With 1-methyl-pyrrolidin-2-one; hydrogenchloride; N-iodo-succinimide; copper(l) iodide; sulfuric acid; potassium tert-butylate; nitric acid; sodium hexamethyldisilazane; ammonium chloride; caesium carbonate; diisopropylamine; 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-1-methyl-7-(2-phenylethynyl)-1H-imidazo[4,5-c]pyridin-4-yl(methyl)carbamate

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

acetophenone

pyridin-4-ol