4-{3-[6-(2,4-difluoro-phenylamino)-1-(2-trimethylsilanyl-ethoxymethyl)-1H-pyrazolo[3,4-b]pyridin-3-yl]-4-methoxy-benzoyl}-piperazine-1-carboxylic acid tert-butyl ester

Base Information

• Chemical Name: 4-{3-[6-(2,4-difluoro-phenylamino)-1-(2-trimethylsilanyl-ethoxymethyl)-1H-pyrazolo[3,4-b]pyridin-3-yl]-4-methoxy-benzoyl}-piperazine-1-carboxylic acid tert-butyl ester
• CAS No.: 919079-57-5
• Molecular Formula: C₃₅H₄₄F₂N₆O₅Si
• Molecular Weight: 694.854

Synonyms:

Chemical Property of 4-{3-[6-(2,4-difluoro-phenylamino)-1-(2-trimethylsilanyl-ethoxymethyl)-1H-pyrazolo[3,4-b]pyridin-3-yl]-4-methoxy-benzoyl}-piperazine-1-carboxylic acid tert-butyl ester

Chemical Property:

Purity/Quality:

Safty Information:

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Useful:

Technology Process of 4-{3-[6-(2,4-difluoro-phenylamino)-1-(2-trimethylsilanyl-ethoxymethyl)-1H-pyrazolo[3,4-b]pyridin-3-yl]-4-methoxy-benzoyl}-piperazine-1-carboxylic acid tert-butyl ester

There total 9 articles about 4-{3-[6-(2,4-difluoro-phenylamino)-1-(2-trimethylsilanyl-ethoxymethyl)-1H-pyrazolo[3,4-b]pyridin-3-yl]-4-methoxy-benzoyl}-piperazine-1-carboxylic acid tert-butyl 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:

(5-bromo-2-methoxy-phenyl)-(2,6-dichloro-pyridin-3-yl)-methanone (872513-21-8) → 4-{3-[6-(2,4-difluoro-phenylamino)-1-(2-trimethylsilanyl-ethoxymethyl)-1H-pyrazolo[3,4-b]pyridin-3-yl]-4-methoxy-benzoyl}-piperazine-1-carboxylic acid tert-butyl ester (919079-57-5)

Guidance literature:

Multi-step reaction with 5 steps

1.1: 70 percent / hydrazine hydrate / ethanol; butan-1-ol / 1 h / Heating

2.1: KN(TMS)2 / tetrahydrofuran / -78 °C

3.1: n-BuLi / tetrahydrofuran

3.2: 63 percent / tetrahydrofuran

4.1: 96 percent / PPh₃; NaOtBu; R-(+)-BINAP / Pd(OAc)2 / dioxane / 0.25 h / Heating

5.1: 1,1'-carbonyldiimidazole / tetrahydrofuran / 0.17 h / Heating

With n-butyllithium; potassium hexamethylsilazane; hydrazine hydrate; (R)-2,2'-bis(diphenylphosphanyl)-1,1'-binaphthyl; triphenylphosphine; 1,1'-carbonyldiimidazole; sodium t-butanolate; palladium diacetate; In tetrahydrofuran; 1,4-dioxane; ethanol; butan-1-ol; 4.1: Buchwald reaction;

DOI:10.1016/j.bmcl.2005.10.015

Reference yield:

(5-bromo-2-methoxy-phenyl)-(2,6-dichloro-pyridin-3-yl)-methanol (872513-52-5) → 4-{3-[6-(2,4-difluoro-phenylamino)-1-(2-trimethylsilanyl-ethoxymethyl)-1H-pyrazolo[3,4-b]pyridin-3-yl]-4-methoxy-benzoyl}-piperazine-1-carboxylic acid tert-butyl ester (919079-57-5)

Guidance literature:

Multi-step reaction with 6 steps

1.1: 79 percent / CrO₃; aq. H₂SO₄ / acetone

2.1: 70 percent / hydrazine hydrate / ethanol; butan-1-ol / 1 h / Heating

3.1: KN(TMS)2 / tetrahydrofuran / -78 °C

4.1: n-BuLi / tetrahydrofuran

4.2: 63 percent / tetrahydrofuran

5.1: 96 percent / PPh₃; NaOtBu; R-(+)-BINAP / Pd(OAc)2 / dioxane / 0.25 h / Heating

6.1: 1,1'-carbonyldiimidazole / tetrahydrofuran / 0.17 h / Heating

With chromium(VI) oxide; n-butyllithium; sulfuric acid; potassium hexamethylsilazane; hydrazine hydrate; (R)-2,2'-bis(diphenylphosphanyl)-1,1'-binaphthyl; triphenylphosphine; 1,1'-carbonyldiimidazole; sodium t-butanolate; palladium diacetate; In tetrahydrofuran; 1,4-dioxane; ethanol; acetone; butan-1-ol; 1.1: Jones oxidation / 5.1: Buchwald reaction;

DOI:10.1016/j.bmcl.2005.10.015

Reference yield:

3-(5-bromo-2-methoxy-phenyl)-6-chloro-1H-pyrazolo[3,4-b]pyridine (872513-22-9) → 4-{3-[6-(2,4-difluoro-phenylamino)-1-(2-trimethylsilanyl-ethoxymethyl)-1H-pyrazolo[3,4-b]pyridin-3-yl]-4-methoxy-benzoyl}-piperazine-1-carboxylic acid tert-butyl ester (919079-57-5)

Guidance literature:

Multi-step reaction with 4 steps

1.1: KN(TMS)2 / tetrahydrofuran / -78 °C

2.1: n-BuLi / tetrahydrofuran

2.2: 63 percent / tetrahydrofuran

3.1: 96 percent / PPh₃; NaOtBu; R-(+)-BINAP / Pd(OAc)2 / dioxane / 0.25 h / Heating

4.1: 1,1'-carbonyldiimidazole / tetrahydrofuran / 0.17 h / Heating

With n-butyllithium; potassium hexamethylsilazane; (R)-2,2'-bis(diphenylphosphanyl)-1,1'-binaphthyl; triphenylphosphine; 1,1'-carbonyldiimidazole; sodium t-butanolate; palladium diacetate; In tetrahydrofuran; 1,4-dioxane; 3.1: Buchwald reaction;

DOI:10.1016/j.bmcl.2005.10.015

upstream raw materials:

3-[6-(2,4-difluoro-phenylamino)-1-(2-trimethylsilanyl-ethoxymethyl)-1H-pyrazolo[3,4-b]pyridin-3-yl]-4-methoxy-benzoic acid

1-t-Butoxycarbonylpiperazine

(5-bromo-2-methoxy-phenyl)-(2,6-dichloro-pyridin-3-yl)-methanone

(5-bromo-2-methoxy-phenyl)-(2,6-dichloro-pyridin-3-yl)-methanol

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