1-(2,2-dimethylpropyl)-5-[5-(2-hydroxypropan-2-yl)-2-methylphenyl]-3-methyl-1,3-dihydro-2H-imidazo[4,5-b]pyridin-2-one

Base Information

• Chemical Name: 1-(2,2-dimethylpropyl)-5-[5-(2-hydroxypropan-2-yl)-2-methylphenyl]-3-methyl-1,3-dihydro-2H-imidazo[4,5-b]pyridin-2-one
• CAS No.: 1352421-24-9
• Molecular Formula: C₂₂H₂₉N₃O₂
• Molecular Weight: 367.491

Synonyms:1-(2,2-dimethylpropyl)-5-[5-(2-hydroxypropan-2-yl)-2-methylphenyl]-3-methyl-1,3-dihydro-2H-imidazo[4,5-b]pyridin-2-one

Chemical Property of 1-(2,2-dimethylpropyl)-5-[5-(2-hydroxypropan-2-yl)-2-methylphenyl]-3-methyl-1,3-dihydro-2H-imidazo[4,5-b]pyridin-2-one

Chemical Property:

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Technology Process of 1-(2,2-dimethylpropyl)-5-[5-(2-hydroxypropan-2-yl)-2-methylphenyl]-3-methyl-1,3-dihydro-2H-imidazo[4,5-b]pyridin-2-one

There total 7 articles about 1-(2,2-dimethylpropyl)-5-[5-(2-hydroxypropan-2-yl)-2-methylphenyl]-3-methyl-1,3-dihydro-2H-imidazo[4,5-b]pyridin-2-one 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%

2-(3-bromo-4-methylphenyl)propan-2-ol (1345961-02-5) + 5-chloro-1-(2,2-dimethylpropyl)-3-methyl-1,3-dihydro-2H-imidazo[4,5-b]pyridin-2-one (1276676-86-8) → 1-(2,2-dimethylpropyl)-5-[5-(2-hydroxypropan-2-yl)-2-methylphenyl]-3-methyl-1,3-dihydro-2H-imidazo[4,5-b]pyridin-2-one (1352421-24-9)

Guidance literature:

With dicyclohexyl-(2',6'-dimethoxybiphenyl-2-yl)-phosphane; potassium phosphate; palladium diacetate; In tetrahydrofuran; water; at 66 ℃; Inert atmosphere;

DOI:10.1016/j.bmcl.2016.01.021

Reference yield:

6-chloro-N-methyl-3-nitropyridin-2-amine (33742-70-0) → 1-(2,2-dimethylpropyl)-5-[5-(2-hydroxypropan-2-yl)-2-methylphenyl]-3-methyl-1,3-dihydro-2H-imidazo[4,5-b]pyridin-2-one (1352421-24-9)

Guidance literature:

Multi-step reaction with 4 steps

1: tin(II) chloride dihdyrate; hydrogenchloride / water / 18 h / Reflux

2: N,N-dimethyl-formamide / 18 h / 80 °C

3: caesium carbonate / 1-methyl-pyrrolidin-2-one / 15 h / 90 °C

4: palladium diacetate; dicyclohexyl-(2',6'-dimethoxybiphenyl-2-yl)-phosphane; potassium phosphate / water; tetrahydrofuran / 66 °C / Inert atmosphere

With dicyclohexyl-(2',6'-dimethoxybiphenyl-2-yl)-phosphane; hydrogenchloride; potassium phosphate; tin(II) chloride dihdyrate; palladium diacetate; caesium carbonate; In tetrahydrofuran; 1-methyl-pyrrolidin-2-one; water; N,N-dimethyl-formamide; 4: |Suzuki Coupling;

DOI:10.1016/j.bmcl.2016.01.021

Reference yield:

2,6-dicholoro-3-nitropyridine (16013-85-7,136901-10-5) → 1-(2,2-dimethylpropyl)-5-[5-(2-hydroxypropan-2-yl)-2-methylphenyl]-3-methyl-1,3-dihydro-2H-imidazo[4,5-b]pyridin-2-one (1352421-24-9)

Guidance literature:

Multi-step reaction with 5 steps

1: sodium carbonate / ethanol; methanol / 3 h / 20 °C

2: tin(II) chloride dihdyrate; hydrogenchloride / water / 18 h / Reflux

3: N,N-dimethyl-formamide / 18 h / 80 °C

4: caesium carbonate / 1-methyl-pyrrolidin-2-one / 15 h / 90 °C

5: palladium diacetate; dicyclohexyl-(2',6'-dimethoxybiphenyl-2-yl)-phosphane; potassium phosphate / water; tetrahydrofuran / 66 °C / Inert atmosphere

With dicyclohexyl-(2',6'-dimethoxybiphenyl-2-yl)-phosphane; hydrogenchloride; potassium phosphate; tin(II) chloride dihdyrate; palladium diacetate; sodium carbonate; caesium carbonate; In tetrahydrofuran; 1-methyl-pyrrolidin-2-one; methanol; ethanol; water; N,N-dimethyl-formamide; 5: |Suzuki Coupling;

DOI:10.1016/j.bmcl.2016.01.021

upstream raw materials:

6-chloro-N-methyl-3-nitropyridin-2-amine

6-chloro-N²-methylpyridine-2,3-diamine

5-chloro-3-methyl-1,3-dihydro-2H-imidazo[4,5-b]pyridin-2-one

2-(3-bromo-4-methylphenyl)propan-2-ol

Downstream raw materials:

5-[5-(1-azido-1-methylethyl)-2-methylphenyl]-1-(2,2-dimethylpropyl)-3-methyl-1,3-dihydro-2H-imidazo[4,5-b]pyridin-2-one

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