3-fluoro-4-(1-methyl-6-(1H-pyrazol-4-yl)-1H-indazol-5-yloxy)aniline

Base Information

• Chemical Name: 3-fluoro-4-(1-methyl-6-(1H-pyrazol-4-yl)-1H-indazol-5-yloxy)aniline
• CAS No.: 1206800-67-0
• Molecular Formula: C₁₇H₁₄FN₅O
• Molecular Weight: 323.329
• Mol file: 1206800-67-0.mol

Synonyms:3-fluoro-4-(1-methyl-6-(1H-pyrazol-4-yl)-1H-indazol-5-yloxy)aniline

Chemical Property of 3-fluoro-4-(1-methyl-6-(1H-pyrazol-4-yl)-1H-indazol-5-yloxy)aniline

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 3-fluoro-4-(1-methyl-6-(1H-pyrazol-4-yl)-1H-indazol-5-yloxy)aniline

There total 23 articles about 3-fluoro-4-(1-methyl-6-(1H-pyrazol-4-yl)-1H-indazol-5-yloxy)aniline 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:

2-methyl-4-methoxyaniline (102-50-1) → 3-fluoro-4-(1-methyl-6-(1H-pyrazol-4-yl)-1H-indazol-5-yloxy)aniline (1206800-67-0)

Guidance literature:

Multi-step reaction with 11 steps

1.1: dichloromethane / 3 h / 25 °C / Large scale

2.1: acetic acid; bromine / 10 h / 8 - 30 °C / Large scale

3.1: hydrogenchloride / methanol; water / Reflux; Large scale

4.1: hydrogenchloride; sodium nitrite / water / 0.5 h / 0 °C / Large scale

4.2: 1 h / 0 - 5 °C / Large scale

4.3: 25 °C / Inert atmosphere; Large scale

5.1: potassium tert-butylate / tetrahydrofuran / 2.5 h / 20 - 25 °C / Large scale

6.1: aluminum (III) chloride / toluene / 5 h / 110 °C / Large scale

6.2: Large scale

7.1: sodium hydrogencarbonate / N,N-dimethyl-formamide / 15 h / 60 - 65 °C / Large scale

8.1: potassium phosphate monohydrate; di-tert-butyl dicarbonate; dichloro[1,1'-bis(di-t-butylphosphino)ferrocene]palladium(II) / water; tetrahydrofuran / 20 h / 20 - 40 °C / Large scale

9.1: palladium 10% on activated carbon; hydrogen / tetrahydrofuran / 45 h / 2585.81 Torr / Large scale

10.1: N-ethyl-N,N-diisopropylamine; benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride / N,N-dimethyl-formamide / 24 h / 20 °C

11.1: hydrogenchloride / water

With hydrogenchloride; aluminum (III) chloride; potassium phosphate monohydrate; dichloro[1,1'-bis(di-t-butylphosphino)ferrocene]palladium(II); di-tert-butyl dicarbonate; palladium 10% on activated carbon; potassium tert-butylate; hydrogen; bromine; sodium hydrogencarbonate; benzotriazol-1-ol; acetic acid; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; N-ethyl-N,N-diisopropylamine; sodium nitrite; In tetrahydrofuran; methanol; dichloromethane; water; N,N-dimethyl-formamide; toluene; 8.1: |Suzuki Coupling;

DOI:10.1021/op400317z

Reference yield:

N-(4-methoxy-2-methylphenyl)acetamide (31601-41-9) → 3-fluoro-4-(1-methyl-6-(1H-pyrazol-4-yl)-1H-indazol-5-yloxy)aniline (1206800-67-0)

Guidance literature:

Multi-step reaction with 10 steps

1.1: acetic acid; bromine / 10 h / 8 - 30 °C / Large scale

2.1: hydrogenchloride / methanol; water / Reflux; Large scale

3.1: hydrogenchloride; sodium nitrite / water / 0.5 h / 0 °C / Large scale

3.2: 1 h / 0 - 5 °C / Large scale

3.3: 25 °C / Inert atmosphere; Large scale

4.1: potassium tert-butylate / tetrahydrofuran / 2.5 h / 20 - 25 °C / Large scale

5.1: aluminum (III) chloride / toluene / 5 h / 110 °C / Large scale

5.2: Large scale

6.1: sodium hydrogencarbonate / N,N-dimethyl-formamide / 15 h / 60 - 65 °C / Large scale

7.1: potassium phosphate monohydrate; di-tert-butyl dicarbonate; dichloro[1,1'-bis(di-t-butylphosphino)ferrocene]palladium(II) / water; tetrahydrofuran / 20 h / 20 - 40 °C / Large scale

8.1: palladium 10% on activated carbon; hydrogen / tetrahydrofuran / 45 h / 2585.81 Torr / Large scale

9.1: N-ethyl-N,N-diisopropylamine; benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride / N,N-dimethyl-formamide / 24 h / 20 °C

10.1: hydrogenchloride / water

With hydrogenchloride; aluminum (III) chloride; potassium phosphate monohydrate; dichloro[1,1'-bis(di-t-butylphosphino)ferrocene]palladium(II); di-tert-butyl dicarbonate; palladium 10% on activated carbon; potassium tert-butylate; hydrogen; bromine; sodium hydrogencarbonate; benzotriazol-1-ol; acetic acid; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; N-ethyl-N,N-diisopropylamine; sodium nitrite; In tetrahydrofuran; methanol; water; N,N-dimethyl-formamide; toluene; 7.1: |Suzuki Coupling;

DOI:10.1021/op400317z

Reference yield:

5-bromo-4-methoxy-2-methylbenzenamine (861084-04-0) → 3-fluoro-4-(1-methyl-6-(1H-pyrazol-4-yl)-1H-indazol-5-yloxy)aniline (1206800-67-0)

Guidance literature:

Multi-step reaction with 10 steps

1.1: hydrogenchloride; sodium nitrite / water / 0.5 h / 0 °C / Large scale

1.2: 1 h / 0 - 5 °C / Large scale

1.3: 25 °C / Inert atmosphere; Large scale

2.1: boron tribromide / dichloromethane

3.1: methanesulfonic acid / tetrahydrofuran

4.1: sodium hydrogencarbonate / N,N-dimethyl-formamide / 70 °C

5.1: methanesulfonic acid / methanol / 24 h / 50 °C

6.1: potassium carbonate / N,N-dimethyl-formamide / 24 h / 0 - 20 °C

7.1: potassium phosphate monohydrate; di-tert-butyl dicarbonate; dichloro[1,1'-bis(di-t-butylphosphino)ferrocene]palladium(II) / water; tetrahydrofuran / 20 h / 20 - 40 °C / Large scale

8.1: palladium 10% on activated carbon; hydrogen / tetrahydrofuran / 45 h / 2585.81 Torr / Large scale

9.1: N-ethyl-N,N-diisopropylamine; benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride / N,N-dimethyl-formamide / 24 h / 20 °C

10.1: hydrogenchloride / water

With hydrogenchloride; potassium phosphate monohydrate; dichloro[1,1'-bis(di-t-butylphosphino)ferrocene]palladium(II); methanesulfonic acid; di-tert-butyl dicarbonate; palladium 10% on activated carbon; hydrogen; boron tribromide; sodium hydrogencarbonate; potassium carbonate; benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; N-ethyl-N,N-diisopropylamine; sodium nitrite; In tetrahydrofuran; methanol; dichloromethane; water; N,N-dimethyl-formamide; 7.1: |Suzuki Coupling;

DOI:10.1021/op400317z

upstream raw materials:

tert-butyl 4-(5-(2-fluoro-4-nitrophenoxy)-1-methyl-1H-indazol-6-yl)-1H-pyrazole-1-carboxylate

tert-butyl 4-(5-(4-amino-2-fluorophenoxy)-1-methyl-1H-indazol-6-yl)-1H-pyrazole-1-carboxylate

tert-butyl 4-(5-(2-fluoro-4-(1-(4-fluorophenyl)-6-methyl-2-oxo-1,2-dihydropyridine-3-carboxamido)phenoxy)-1-methyl-1H-indazol-6-yl)-1H-pyrazole-1-carboxylate

6-bromo-5-methoxy-1-methyl-1H-indazole

Downstream raw materials:

N-(3-fluoro-4-(1-methyl-6-(1H-pyrazol-4-yl)-1H-indazol-5-yloxy)phenyl)-1-(4-fluorophenyl)-4,6-dimethyl-2-oxo-1,2-dihydropyridine-3-carboxamide