5-benzyloxy-1,2,4,6-tetramethyl-2,3-dihydro-1H-pyrrolo[2,3-b]pyridine-2-carbaldehyde

Base Information

Chemical Name:5-benzyloxy-1,2,4,6-tetramethyl-2,3-dihydro-1H-pyrrolo[2,3-b]pyridine-2-carbaldehyde
CAS No.:1287234-58-5
Molecular Formula:C₁₉H₂₂N₂O₂
Molecular Weight:310.396
Hs Code.:

Synonyms:5-benzyloxy-1,2,4,6-tetramethyl-2,3-dihydro-1H-pyrrolo[2,3-b]pyridine-2-carbaldehyde

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Chemical Property of 5-benzyloxy-1,2,4,6-tetramethyl-2,3-dihydro-1H-pyrrolo[2,3-b]pyridine-2-carbaldehyde

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Technology Process of 5-benzyloxy-1,2,4,6-tetramethyl-2,3-dihydro-1H-pyrrolo[2,3-b]pyridine-2-carbaldehyde

There total 10 articles about 5-benzyloxy-1,2,4,6-tetramethyl-2,3-dihydro-1H-pyrrolo[2,3-b]pyridine-2-carbaldehyde 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: 93.0%

: 1287234-57-4
tert-butyl 5-benzyloxy-1,2,4,6-tetramethyl-2,3-dihydro-1H-pyrrolo[2,3-b]pyridine-2-carboxylate

: 1287234-58-5
5-benzyloxy-1,2,4,6-tetramethyl-2,3-dihydro-1H-pyrrolo[2,3-b]pyridine-2-carbaldehyde

Guidance literature:: With diisobutylaluminium hydride; In dichloromethane; at -78 ℃; for 0.5h;
DOI:10.1039/c0ob00991a

Reference yield:

: 1287234-51-8
6-bromo-2,4-dimethyl-5-acetoxymethyl-3-benzyloxypyridine

: 1287234-58-5
5-benzyloxy-1,2,4,6-tetramethyl-2,3-dihydro-1H-pyrrolo[2,3-b]pyridine-2-carbaldehyde

Guidance literature:: Multi-step reaction with 7 steps

1: sodium methylate / methanol / 0.5 h / 20 °C

2: thionyl chloride / chloroform / 0.17 h / 20 °C

3: tetrabutylammomium bromide; potassium hydroxide / dichloromethane / 2 h / 20 °C

4: hydrogenchloride; water / tetrahydrofuran / 1 h / 20 °C

5: potassium phosphate; N,N-diethylsalicylamide; copper (I) acetate / N,N-dimethyl-formamide / 10 h / 80 °C

6: sodium cyanoborohydride; acetic acid / methanol; water / 6 h / 20 °C

7: diisobutylaluminium hydride / dichloromethane / 0.5 h / -78 °C

With hydrogenchloride; potassium phosphate; thionyl chloride; N,N-diethylsalicylamide; tetrabutylammomium bromide; water; sodium methylate; copper (I) acetate; diisobutylaluminium hydride; sodium cyanoborohydride; acetic acid; potassium hydroxide; In tetrahydrofuran; methanol; dichloromethane; chloroform; water; N,N-dimethyl-formamide; 5: Buchwald amination;
DOI:10.1039/c0ob00991a

Reference yield:

: 1287234-50-7
6-bromo-2,4-dimethyl-5-acetoxymethyl-3-hydroxypyridine

: 1287234-58-5
5-benzyloxy-1,2,4,6-tetramethyl-2,3-dihydro-1H-pyrrolo[2,3-b]pyridine-2-carbaldehyde

Guidance literature:: Multi-step reaction with 8 steps

1: sodium hydride / tetrahydrofuran / 2 h / Reflux

2: sodium methylate / methanol / 0.5 h / 20 °C

3: thionyl chloride / chloroform / 0.17 h / 20 °C

4: tetrabutylammomium bromide; potassium hydroxide / dichloromethane / 2 h / 20 °C

5: hydrogenchloride; water / tetrahydrofuran / 1 h / 20 °C

6: potassium phosphate; N,N-diethylsalicylamide; copper (I) acetate / N,N-dimethyl-formamide / 10 h / 80 °C

7: sodium cyanoborohydride; acetic acid / methanol; water / 6 h / 20 °C

8: diisobutylaluminium hydride / dichloromethane / 0.5 h / -78 °C

With hydrogenchloride; potassium phosphate; thionyl chloride; N,N-diethylsalicylamide; tetrabutylammomium bromide; water; sodium methylate; copper (I) acetate; sodium hydride; diisobutylaluminium hydride; sodium cyanoborohydride; acetic acid; potassium hydroxide; In tetrahydrofuran; methanol; dichloromethane; chloroform; water; N,N-dimethyl-formamide; 6: Buchwald amination;
DOI:10.1039/c0ob00991a