3-amino-2-(7'-bromo-8'-hydroxyquinolin-2'-yl)-4-(3',4'-dimethoxy-2'-hydroxyphenyl)-6-methoxy-5-methylpyridine

Base Information

Chemical Name:3-amino-2-(7'-bromo-8'-hydroxyquinolin-2'-yl)-4-(3',4'-dimethoxy-2'-hydroxyphenyl)-6-methoxy-5-methylpyridine
CAS No.:152455-84-0
Molecular Formula:C₂₄H₂₂BrN₃O₅
Molecular Weight:512.36
Hs Code.:

Synonyms:3-amino-2-(7'-bromo-8'-hydroxyquinolin-2'-yl)-4-(3',4'-dimethoxy-2'-hydroxyphenyl)-6-methoxy-5-methylpyridine

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Chemical Property of 3-amino-2-(7'-bromo-8'-hydroxyquinolin-2'-yl)-4-(3',4'-dimethoxy-2'-hydroxyphenyl)-6-methoxy-5-methylpyridine

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Technology Process of 3-amino-2-(7'-bromo-8'-hydroxyquinolin-2'-yl)-4-(3',4'-dimethoxy-2'-hydroxyphenyl)-6-methoxy-5-methylpyridine

There total 16 articles about 3-amino-2-(7'-bromo-8'-hydroxyquinolin-2'-yl)-4-(3',4'-dimethoxy-2'-hydroxyphenyl)-6-methoxy-5-methylpyridine 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:

: 19283-70-6
3,4-dimethoxysalicylaldehyde

: 152455-84-0
3-amino-2-(7'-bromo-8'-hydroxyquinolin-2'-yl)-4-(3',4'-dimethoxy-2'-hydroxyphenyl)-6-methoxy-5-methylpyridine

Guidance literature:: Multi-step reaction with 9 steps

1: 81 percent / piperidine / ethanol / 1 h / Heating

2: 75 percent / TiCl₄, Et₃N / CH₂Cl₂ / 6.5 h / 0 - 25 °C

3: t-BuOK / benzene / 3 h / 24 °C

4: DDQ / tetrahydrofuran / 1 h / -30 °C

5: 92 percent / Na₂CO₃ / tetrahydrofuran / 4 h / 25 °C

6: 81 percent / i-Pr₂NEt / CHCl₃ / 6 h / Heating

7: 42 percent / 4 N aq. LiOH / dimethylsulfoxide / 26 h / 130 - 135 °C

8: 1.) Et₃N, diphenyl phosphorazidate, 2.) 4 N aq. LiOH / 1.) benzene, a) 25 deg C, 15 min, b) reflux, 7 h, 2.) 25 deg C, 1 h

9: 80 percent / HgBr(g) / CH₂Cl₂ / 2 h / 0 °C

With piperidine; lithium hydroxide; diphenyl phosphoryl azide; potassium tert-butylate; mercury(I) bromide; titanium tetrachloride; sodium carbonate; triethylamine; N-ethyl-N,N-diisopropylamine; 2,3-dicyano-5,6-dichloro-p-benzoquinone; In tetrahydrofuran; ethanol; dichloromethane; chloroform; dimethyl sulfoxide; benzene;
DOI:10.1021/ja00076a035

Reference yield:

: 495409-83-1
8-benzyloxy-7-bromo-quinoline-2-carboxylic acid

: 152455-84-0
3-amino-2-(7'-bromo-8'-hydroxyquinolin-2'-yl)-4-(3',4'-dimethoxy-2'-hydroxyphenyl)-6-methoxy-5-methylpyridine

Guidance literature:: Multi-step reaction with 11 steps

1: HCl / 5 h / 24 °C

2: 1.) LDA / 1.) THF, hexane, -78 deg C, 15 min, 2.) THF, hexane, -78 deg C, 40 min

3: 81 percent / piperidine / ethanol / 1 h / Heating

4: 75 percent / TiCl₄, Et₃N / CH₂Cl₂ / 6.5 h / 0 - 25 °C

5: t-BuOK / benzene / 3 h / 24 °C

6: DDQ / tetrahydrofuran / 1 h / -30 °C

7: 92 percent / Na₂CO₃ / tetrahydrofuran / 4 h / 25 °C

8: 81 percent / i-Pr₂NEt / CHCl₃ / 6 h / Heating

9: 42 percent / 4 N aq. LiOH / dimethylsulfoxide / 26 h / 130 - 135 °C

10: 1.) Et₃N, diphenyl phosphorazidate, 2.) 4 N aq. LiOH / 1.) benzene, a) 25 deg C, 15 min, b) reflux, 7 h, 2.) 25 deg C, 1 h

11: 80 percent / HgBr(g) / CH₂Cl₂ / 2 h / 0 °C

With piperidine; hydrogenchloride; lithium hydroxide; diphenyl phosphoryl azide; potassium tert-butylate; mercury(I) bromide; titanium tetrachloride; sodium carbonate; triethylamine; N-ethyl-N,N-diisopropylamine; 2,3-dicyano-5,6-dichloro-p-benzoquinone; lithium diisopropyl amide; In tetrahydrofuran; ethanol; dichloromethane; chloroform; dimethyl sulfoxide; benzene;
DOI:10.1021/ja00076a035

Reference yield:

: 99573-20-3
2-Amino-3-(benzyloxy)-4-bromobenzaldehyde

: 152455-84-0
3-amino-2-(7'-bromo-8'-hydroxyquinolin-2'-yl)-4-(3',4'-dimethoxy-2'-hydroxyphenyl)-6-methoxy-5-methylpyridine

Guidance literature:: Multi-step reaction with 12 steps

1: NaOH / methanol / 6 h / 57 °C

2: HCl / 5 h / 24 °C

3: 1.) LDA / 1.) THF, hexane, -78 deg C, 15 min, 2.) THF, hexane, -78 deg C, 40 min

4: 81 percent / piperidine / ethanol / 1 h / Heating

5: 75 percent / TiCl₄, Et₃N / CH₂Cl₂ / 6.5 h / 0 - 25 °C

6: t-BuOK / benzene / 3 h / 24 °C

7: DDQ / tetrahydrofuran / 1 h / -30 °C

8: 92 percent / Na₂CO₃ / tetrahydrofuran / 4 h / 25 °C

9: 81 percent / i-Pr₂NEt / CHCl₃ / 6 h / Heating

10: 42 percent / 4 N aq. LiOH / dimethylsulfoxide / 26 h / 130 - 135 °C

11: 1.) Et₃N, diphenyl phosphorazidate, 2.) 4 N aq. LiOH / 1.) benzene, a) 25 deg C, 15 min, b) reflux, 7 h, 2.) 25 deg C, 1 h

12: 80 percent / HgBr(g) / CH₂Cl₂ / 2 h / 0 °C

With piperidine; hydrogenchloride; lithium hydroxide; sodium hydroxide; diphenyl phosphoryl azide; potassium tert-butylate; mercury(I) bromide; titanium tetrachloride; sodium carbonate; triethylamine; N-ethyl-N,N-diisopropylamine; 2,3-dicyano-5,6-dichloro-p-benzoquinone; lithium diisopropyl amide; In tetrahydrofuran; methanol; ethanol; dichloromethane; chloroform; dimethyl sulfoxide; benzene;
DOI:10.1021/ja00076a035