N-[6-(3-hydroxyphenyl)-1H-indazol-4-yl]-2-methyl-1,3-thiazole-4-carboxamide

Base Information

Chemical Name:N-[6-(3-hydroxyphenyl)-1H-indazol-4-yl]-2-methyl-1,3-thiazole-4-carboxamide
CAS No.:1198804-07-7
Molecular Formula:C₁₈H₁₄N₄O₂S
Molecular Weight:350.401
Hs Code.:

Synonyms:N-[6-(3-hydroxyphenyl)-1H-indazol-4-yl]-2-methyl-1,3-thiazole-4-carboxamide

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Chemical Property of N-[6-(3-hydroxyphenyl)-1H-indazol-4-yl]-2-methyl-1,3-thiazole-4-carboxamide

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Technology Process of N-[6-(3-hydroxyphenyl)-1H-indazol-4-yl]-2-methyl-1,3-thiazole-4-carboxamide

There total 9 articles about N-[6-(3-hydroxyphenyl)-1H-indazol-4-yl]-2-methyl-1,3-thiazole-4-carboxamide 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:

: 591-20-8
3-Bromophenol

: 1198437-65-8
2-methyl-N-[2-(tetrahydro-2H-pyran-2-yl)-6-(4,4,6,6-tetramethyl-1,3,2-dioxaborinan-2-yl)-2H-indazol-4-yl]-1,3-thiazole-4-carboxamide

: 76-05-1
trifluoroacetic acid

: 1198804-07-7
N-[6-(3-hydroxyphenyl)-1H-indazol-4-yl]-2-methyl-1,3-thiazole-4-carboxamide

Guidance literature:: 3-Bromophenol; 2-methyl-N-[2-(tetrahydro-2H-pyran-2-yl)-6-(4,4,6,6-tetramethyl-1,3,2-dioxaborinan-2-yl)-2H-indazol-4-yl]-1,3-thiazole-4-carboxamide; With sodium carbonate; (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; In 1,4-dioxane; water; at 140 ℃; for 0.333333h; Microwave irradiation;

trifluoroacetic acid; In methanol; water; dimethyl sulfoxide; acetonitrile;

Reference yield:

: 885518-46-7
6-bromo-4-nitro-1H-indazole

: 1198804-07-7
N-[6-(3-hydroxyphenyl)-1H-indazol-4-yl]-2-methyl-1,3-thiazole-4-carboxamide

Guidance literature:: Multi-step reaction with 6 steps

1: trifluoroacetic acid / 1.5 h / Reflux

2: iron; ammonium chloride / ethanol; water / 2.5 h / 80 °C

3: pyridine / dichloromethane / 1 h / 20 °C

4: (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium acetate / 1,4-dioxane / 1 h / 80 °C / Microwave irradiation

5: (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; sodium carbonate / water; 1,4-dioxane / 0.33 h / 140 °C / Microwave irradiation

6: trifluoroacetic acid / Sonication

With pyridine; (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium acetate; iron; sodium carbonate; ammonium chloride; trifluoroacetic acid; In 1,4-dioxane; ethanol; dichloromethane; water; 4: |Miyaura Borylation Reaction / 5: |Suzuki-Miyaura Coupling;
DOI:10.1021/acs.jmedchem.5b00767

Reference yield:

: 1198409-38-9
6-bromo-4-nitro-2-(tetrahydro-2H-pyran-2-yl)-2H-indazole

: 1198804-07-7
N-[6-(3-hydroxyphenyl)-1H-indazol-4-yl]-2-methyl-1,3-thiazole-4-carboxamide

Guidance literature:: Multi-step reaction with 5 steps

1: iron; ammonium chloride / ethanol; water / 2.5 h / 80 °C

2: pyridine / dichloromethane / 1 h / 20 °C

3: (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium acetate / 1,4-dioxane / 1 h / 80 °C / Microwave irradiation

4: (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; sodium carbonate / water; 1,4-dioxane / 0.33 h / 140 °C / Microwave irradiation

5: trifluoroacetic acid / Sonication

With pyridine; (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium acetate; iron; sodium carbonate; ammonium chloride; trifluoroacetic acid; In 1,4-dioxane; ethanol; dichloromethane; water; 3: |Miyaura Borylation Reaction / 4: |Suzuki-Miyaura Coupling;
DOI:10.1021/acs.jmedchem.5b00767