toluene-4-sulfonic acid 3-[2-(4-dimethylamino-phenyl)-imidazo[1,2-a]pyridin-6-yl]-propyl ester

Base Information

• Chemical Name: toluene-4-sulfonic acid 3-[2-(4-dimethylamino-phenyl)-imidazo[1,2-a]pyridin-6-yl]-propyl ester
• CAS No.: 893475-53-1
• Molecular Formula: C₂₅H₂₇N₃O₃S
• Molecular Weight: 449.574

Synonyms:toluene-4-sulfonic acid 3-[2-(4-dimethylamino-phenyl)-imidazo[1,2-a]pyridin-6-yl]-propyl ester

Chemical Property of toluene-4-sulfonic acid 3-[2-(4-dimethylamino-phenyl)-imidazo[1,2-a]pyridin-6-yl]-propyl ester

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Technology Process of toluene-4-sulfonic acid 3-[2-(4-dimethylamino-phenyl)-imidazo[1,2-a]pyridin-6-yl]-propyl ester

There total 6 articles about toluene-4-sulfonic acid 3-[2-(4-dimethylamino-phenyl)-imidazo[1,2-a]pyridin-6-yl]-propyl 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: 52.0%

3-[2-(4-dimethylamino-phenyl)-imidazo[1,2-a]pyridin-6-yl]-propan-1-ol (893475-42-8) + p-toluenesulfonyl chloride (98-59-9) → toluene-4-sulfonic acid 3-[2-(4-dimethylamino-phenyl)-imidazo[1,2-a]pyridin-6-yl]-propyl ester (893475-53-1)

Guidance literature:

With triethylamine; In dichloromethane; at 20 ℃; for 15h;

DOI:10.1016/j.bmcl.2006.02.055

Reference yield:

[4-(6-allyl-imidazo[1,2-a]pyridin-2-yl)-phenyl]-dimethyl-amine (893475-34-8) → toluene-4-sulfonic acid 3-[2-(4-dimethylamino-phenyl)-imidazo[1,2-a]pyridin-6-yl]-propyl ester (893475-53-1)

Guidance literature:

Multi-step reaction with 2 steps

1.1: 9-BBN / tetrahydrofuran / 24 h / 20 °C

1.2: 88 percent / aq. H₂O₂; NaOH / 5 h / 20 °C

2.1: 52 percent / Et₃N / CH₂Cl₂ / 15 h / 20 °C

With 9-borabicyclo[3.3.1]nonane dimer; triethylamine; In tetrahydrofuran; dichloromethane;

DOI:10.1016/j.bmcl.2006.02.055

Reference yield:

[2-Bromo-1-(4-dimethylamino-phenyl)-eth-(Z)-ylidene]-(5-iodo-pyridin-2-yl)-amine → toluene-4-sulfonic acid 3-[2-(4-dimethylamino-phenyl)-imidazo[1,2-a]pyridin-6-yl]-propyl ester (893475-53-1)

Guidance literature:

Multi-step reaction with 4 steps

1.1: NaHCO₃ / ethanol / 5 h / Heating

2.1: 58 percent / (PPh₃)4Pd / toluene / 20 h / 100 °C

3.1: 9-BBN / tetrahydrofuran / 24 h / 20 °C

3.2: 88 percent / aq. H₂O₂; NaOH / 5 h / 20 °C

4.1: 52 percent / Et₃N / CH₂Cl₂ / 15 h / 20 °C

With 9-borabicyclo[3.3.1]nonane dimer; tetrakis(triphenylphosphine) palladium⁽⁰⁾; sodium hydrogencarbonate; triethylamine; In tetrahydrofuran; ethanol; dichloromethane; toluene;

DOI:10.1016/j.bmcl.2006.02.055

upstream raw materials:

3-[2-(4-dimethylamino-phenyl)-imidazo[1,2-a]pyridin-6-yl]-propan-1-ol

p-toluenesulfonyl chloride

[4-(6-allyl-imidazo[1,2-a]pyridin-2-yl)-phenyl]-dimethyl-amine

2-amino-5-iodopyridine

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