methoxymethyl 2-(8'-(benzyloxy)-7'-bromoquinolin-2'-yl)-4-(3',4'-dimethoxy-2'-(methoxymethoxy)phenyl)-6-methoxy-5-methylpyridine-3-carboxylate

Base Information

Chemical Name:methoxymethyl 2-(8'-(benzyloxy)-7'-bromoquinolin-2'-yl)-4-(3',4'-dimethoxy-2'-(methoxymethoxy)phenyl)-6-methoxy-5-methylpyridine-3-carboxylate
CAS No.:152455-81-7
Molecular Formula:C₃₆H₃₅BrN₂O₉
Molecular Weight:719.586
Hs Code.:

Synonyms:methoxymethyl 2-(8'-(benzyloxy)-7'-bromoquinolin-2'-yl)-4-(3',4'-dimethoxy-2'-(methoxymethoxy)phenyl)-6-methoxy-5-methylpyridine-3-carboxylate

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Chemical Property of methoxymethyl 2-(8'-(benzyloxy)-7'-bromoquinolin-2'-yl)-4-(3',4'-dimethoxy-2'-(methoxymethoxy)phenyl)-6-methoxy-5-methylpyridine-3-carboxylate

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Technology Process of methoxymethyl 2-(8'-(benzyloxy)-7'-bromoquinolin-2'-yl)-4-(3',4'-dimethoxy-2'-(methoxymethoxy)phenyl)-6-methoxy-5-methylpyridine-3-carboxylate

There total 11 articles about methoxymethyl 2-(8'-(benzyloxy)-7'-bromoquinolin-2'-yl)-4-(3',4'-dimethoxy-2'-(methoxymethoxy)phenyl)-6-methoxy-5-methylpyridine-3-carboxylate 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

: 152455-81-7
methoxymethyl 2-(8'-(benzyloxy)-7'-bromoquinolin-2'-yl)-4-(3',4'-dimethoxy-2'-(methoxymethoxy)phenyl)-6-methoxy-5-methylpyridine-3-carboxylate

Guidance literature:: Multi-step reaction with 6 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: 97 percent / 4 N aq. LiOH / dimethylsulfoxide / 7 h / 60 °C

6: 1.) NaH / 1.) DMF, 0 deg C, 15 min, 2.) DMF, 25 deg C, 1 h

With piperidine; lithium hydroxide; potassium tert-butylate; titanium tetrachloride; sodium hydride; triethylamine; 2,3-dicyano-5,6-dichloro-p-benzoquinone; In tetrahydrofuran; ethanol; dichloromethane; dimethyl sulfoxide; benzene;
DOI:10.1021/ja00076a035

Reference yield:

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

: 152455-81-7
methoxymethyl 2-(8'-(benzyloxy)-7'-bromoquinolin-2'-yl)-4-(3',4'-dimethoxy-2'-(methoxymethoxy)phenyl)-6-methoxy-5-methylpyridine-3-carboxylate

Guidance literature:: Multi-step reaction with 9 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: 97 percent / 4 N aq. LiOH / dimethylsulfoxide / 7 h / 60 °C

9: 1.) NaH / 1.) DMF, 0 deg C, 15 min, 2.) DMF, 25 deg C, 1 h

With piperidine; hydrogenchloride; lithium hydroxide; sodium hydroxide; potassium tert-butylate; titanium tetrachloride; sodium hydride; triethylamine; 2,3-dicyano-5,6-dichloro-p-benzoquinone; lithium diisopropyl amide; In tetrahydrofuran; methanol; ethanol; dichloromethane; dimethyl sulfoxide; benzene;
DOI:10.1021/ja00076a035

Reference yield:

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

: 152455-81-7
methoxymethyl 2-(8'-(benzyloxy)-7'-bromoquinolin-2'-yl)-4-(3',4'-dimethoxy-2'-(methoxymethoxy)phenyl)-6-methoxy-5-methylpyridine-3-carboxylate

Guidance literature:: Multi-step reaction with 8 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: 97 percent / 4 N aq. LiOH / dimethylsulfoxide / 7 h / 60 °C

8: 1.) NaH / 1.) DMF, 0 deg C, 15 min, 2.) DMF, 25 deg C, 1 h

With piperidine; hydrogenchloride; lithium hydroxide; potassium tert-butylate; titanium tetrachloride; sodium hydride; triethylamine; 2,3-dicyano-5,6-dichloro-p-benzoquinone; lithium diisopropyl amide; In tetrahydrofuran; ethanol; dichloromethane; dimethyl sulfoxide; benzene;
DOI:10.1021/ja00076a035