4-(3-Bromo-phenylamino)-6-fluoro-[1,7]naphthyridine-3-carbonitrile

Base Information

Chemical Name:4-(3-Bromo-phenylamino)-6-fluoro-[1,7]naphthyridine-3-carbonitrile
CAS No.:305371-19-1
Molecular Formula:C₁₅H₈BrFN₄
Molecular Weight:343.158
Hs Code.:
DSSTox Substance ID:DTXSID701166206

Synonyms:SCHEMBL6643911;BRTAOLCKJDDCRL-UHFFFAOYSA-N;DTXSID701166206;4-(3-bromo-phenylamino)-6-fluoro-[1,7]naphthyridine-3-carbonitrile;305371-19-1;4-(3-bromo-phenylamino)-6-fluoro-[1.7]naphthyridine-3-carbonitrile;4-[(3-Bromophenyl)amino]-6-fluoro-1,7-naphthyridine-3-carbonitrile

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Business phase:: The product has achieved commercial mass production^*data from LookChem market partment

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Chemical Property of 4-(3-Bromo-phenylamino)-6-fluoro-[1,7]naphthyridine-3-carbonitrile

Chemical Property:

XLogP3:4.1
Hydrogen Bond Donor Count:1
Hydrogen Bond Acceptor Count:5
Rotatable Bond Count:2
Exact Mass:341.99164
Heavy Atom Count:21
Complexity:412

Purity/Quality:

Safty Information:

Pictogram(s):
Hazard Codes:

MSDS Files:

Useful:

Canonical SMILES:C1=CC(=CC(=C1)Br)NC2=C(C=NC3=CN=C(C=C32)F)C#N

Technology Process of 4-(3-Bromo-phenylamino)-6-fluoro-[1,7]naphthyridine-3-carbonitrile

There total 4 articles about 4-(3-Bromo-phenylamino)-6-fluoro-[1,7]naphthyridine-3-carbonitrile 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: 87.0%

: 591-19-5
m-Bromoaniline

: 305371-18-0
4-chloro-6-fluoro-[1,7]naphthyridine-3-carbonitrile

: 305371-19-1
4-(3-bromo-phenylamino)-6-fluoro-[1.7]naphthyridine-3-carbonitrile

Guidance literature:: In ethanol; for 8h; Heating / reflux;

Reference yield:

: 4548-45-2
2-chloro-5-nitropyridine

: 305371-19-1
4-(3-bromo-phenylamino)-6-fluoro-[1.7]naphthyridine-3-carbonitrile

Guidance literature:: Multi-step reaction with 9 steps

1.1: 84 percent / KF / dimethylsulfoxide / 18 h / 70 °C

2.1: 70 percent / H₂ / Raney Ni / ethyl acetate

3.1: 96 percent / 2-methyl-propan-2-ol / 4 h / 40 °C

4.1: n-BuLi; tetramethylethylenediamine / diethyl ether / -78 °C

4.2: diethyl ether

5.1: methanol; CHCl₃; hexane / 2 h / 0 - 20 °C

6.1: n-BuLi / tetrahydrofuran / 1 h / -78 °C

6.2: AcOH / tetrahydrofuran / -78 - 20 °C

7.1: dimethylformamide / 5 h / 20 °C

8.1: 70 percent / (COCl)2; DMF / CH₂Cl₂ / 2 h / Heating

9.1: ethanol / 8 h / Heating

With potassium fluoride; n-butyllithium; oxalyl dichloride; N,N,N,N,-tetramethylethylenediamine; hydrogen; N,N-dimethyl-formamide; nickel; In tetrahydrofuran; methanol; diethyl ether; ethanol; hexane; dichloromethane; chloroform; dimethyl sulfoxide; ethyl acetate; N,N-dimethyl-formamide; tert-butyl alcohol;
DOI:10.1016/j.bmcl.2004.01.034

Reference yield:

: 456-24-6
2-Fluoro-5-nitropyridine

: 305371-19-1
4-(3-bromo-phenylamino)-6-fluoro-[1.7]naphthyridine-3-carbonitrile

Guidance literature:: Multi-step reaction with 8 steps

1.1: 70 percent / H₂ / Raney Ni / ethyl acetate

2.1: 96 percent / 2-methyl-propan-2-ol / 4 h / 40 °C

3.1: n-BuLi; tetramethylethylenediamine / diethyl ether / -78 °C

3.2: diethyl ether

4.1: methanol; CHCl₃; hexane / 2 h / 0 - 20 °C

5.1: n-BuLi / tetrahydrofuran / 1 h / -78 °C

5.2: AcOH / tetrahydrofuran / -78 - 20 °C

6.1: dimethylformamide / 5 h / 20 °C

7.1: 70 percent / (COCl)2; DMF / CH₂Cl₂ / 2 h / Heating

8.1: ethanol / 8 h / Heating

With n-butyllithium; oxalyl dichloride; N,N,N,N,-tetramethylethylenediamine; hydrogen; N,N-dimethyl-formamide; nickel; In tetrahydrofuran; methanol; diethyl ether; ethanol; hexane; dichloromethane; chloroform; ethyl acetate; N,N-dimethyl-formamide; tert-butyl alcohol;
DOI:10.1016/j.bmcl.2004.01.034