5-(4-fluorobenzyl)-7-methyl-6-oxo-9-(p-tolyl)-1,3,4,5,6,7-hexahydropyrano[3',4':4,5]pyrrolo[2,3-c]pyridine-8-carbaldehyde

Base Information

Chemical Name:5-(4-fluorobenzyl)-7-methyl-6-oxo-9-(p-tolyl)-1,3,4,5,6,7-hexahydropyrano[3',4':4,5]pyrrolo[2,3-c]pyridine-8-carbaldehyde
CAS No.:1428795-20-3
Molecular Formula:C₂₆H₂₃FN₂O₃
Molecular Weight:430.479
Hs Code.:

Synonyms:5-(4-fluorobenzyl)-7-methyl-6-oxo-9-(p-tolyl)-1,3,4,5,6,7-hexahydropyrano[3',4':4,5]pyrrolo[2,3-c]pyridine-8-carbaldehyde

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Chemical Property of 5-(4-fluorobenzyl)-7-methyl-6-oxo-9-(p-tolyl)-1,3,4,5,6,7-hexahydropyrano[3',4':4,5]pyrrolo[2,3-c]pyridine-8-carbaldehyde

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Technology Process of 5-(4-fluorobenzyl)-7-methyl-6-oxo-9-(p-tolyl)-1,3,4,5,6,7-hexahydropyrano[3',4':4,5]pyrrolo[2,3-c]pyridine-8-carbaldehyde

There total 13 articles about 5-(4-fluorobenzyl)-7-methyl-6-oxo-9-(p-tolyl)-1,3,4,5,6,7-hexahydropyrano[3',4':4,5]pyrrolo[2,3-c]pyridine-8-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: 45.3%

: 1428795-17-8
5-(4-fluorobenzyl)-8-(hydroxymethyl)-7-methyl-9-(p-tolyl)-3,4,5,7-tetrahydropyrano[3',4':4,5]pyrrolo[2,3-c]pyridin-6(1H)-one

: 1428795-20-3
5-(4-fluorobenzyl)-7-methyl-6-oxo-9-(p-tolyl)-1,3,4,5,6,7-hexahydropyrano[3',4':4,5]pyrrolo[2,3-c]pyridine-8-carbaldehyde

Guidance literature:: With sodium hydrogencarbonate; Dess-Martin periodane; In dichloromethane; for 2h; Cooling with ice;

Reference yield:

: 1428795-10-1
dimethyl 1-(4-fluorobenzyl)-1,4,6,7-tetrahydropyrano[4,3-b]pyrrole-2,3-dicarboxylate

: 1428795-20-3
5-(4-fluorobenzyl)-7-methyl-6-oxo-9-(p-tolyl)-1,3,4,5,6,7-hexahydropyrano[3',4':4,5]pyrrolo[2,3-c]pyridine-8-carbaldehyde

Guidance literature:: Multi-step reaction with 11 steps

1.1: potassium hydroxide; ethanol / 18 h / 90 °C

2.1: trifluoroacetic anhydride / dichloromethane / 2 h / 20 °C / Cooling with ice

3.1: 2 h / 90 °C / Reflux

4.1: N-ethyl-N,N-diisopropylamine; HATU / N,N-dimethyl-formamide / 0.33 h

5.1: sodium hydride / N,N-dimethyl-formamide / 0.83 h / 20 °C / Cooling with ice

5.2: 0 °C

6.1: triethylamine / dichloromethane / 0.25 h / Cooling with ice

7.1: sodium carbonate; tetrakis(triphenylphosphine) palladium⁽⁰⁾ / water; 1,4-dioxane / 2 h / 80 °C / Inert atmosphere

8.1: lithium hydroxide; methanol / tetrahydrofuran / 18 h / 80 °C / Reflux

8.2: 20 °C

9.1: oxalyl dichloride; N,N-dimethyl-formamide / tetrahydrofuran / 0.25 h

10.1: sodium tetrahydroborate / 1,2-dimethoxyethane / 1 h / 20 °C / Cooling with ice

10.2: 0 °C

11.1: sodium hydrogencarbonate; Dess-Martin periodane / dichloromethane / 2 h / Cooling with ice

With methanol; sodium tetrahydroborate; tetrakis(triphenylphosphine) palladium⁽⁰⁾; oxalyl dichloride; ethanol; sodium hydride; sodium hydrogencarbonate; sodium carbonate; Dess-Martin periodane; triethylamine; N-ethyl-N,N-diisopropylamine; N,N-dimethyl-formamide; HATU; trifluoroacetic anhydride; potassium hydroxide; lithium hydroxide; In tetrahydrofuran; 1,4-dioxane; 1,2-dimethoxyethane; dichloromethane; water; N,N-dimethyl-formamide;

Reference yield:

: 1428795-11-2
dimethyl 1,4,6,7-tetrahydropyrano[4,3-b]pyrrole-2,3-dicarboxylate

: 1428795-20-3
5-(4-fluorobenzyl)-7-methyl-6-oxo-9-(p-tolyl)-1,3,4,5,6,7-hexahydropyrano[3',4':4,5]pyrrolo[2,3-c]pyridine-8-carbaldehyde

Guidance literature:: Multi-step reaction with 12 steps

1.1: caesium carbonate / N,N-dimethyl-formamide / 2 h

2.1: potassium hydroxide; ethanol / 18 h / 90 °C

3.1: trifluoroacetic anhydride / dichloromethane / 2 h / 20 °C / Cooling with ice

4.1: 2 h / 90 °C / Reflux

5.1: N-ethyl-N,N-diisopropylamine; HATU / N,N-dimethyl-formamide / 0.33 h

6.1: sodium hydride / N,N-dimethyl-formamide / 0.83 h / 20 °C / Cooling with ice

6.2: 0 °C

7.1: triethylamine / dichloromethane / 0.25 h / Cooling with ice

8.1: sodium carbonate; tetrakis(triphenylphosphine) palladium⁽⁰⁾ / water; 1,4-dioxane / 2 h / 80 °C / Inert atmosphere

9.1: lithium hydroxide; methanol / tetrahydrofuran / 18 h / 80 °C / Reflux

9.2: 20 °C

10.1: oxalyl dichloride; N,N-dimethyl-formamide / tetrahydrofuran / 0.25 h

11.1: sodium tetrahydroborate / 1,2-dimethoxyethane / 1 h / 20 °C / Cooling with ice

11.2: 0 °C

12.1: sodium hydrogencarbonate; Dess-Martin periodane / dichloromethane / 2 h / Cooling with ice

With methanol; sodium tetrahydroborate; tetrakis(triphenylphosphine) palladium⁽⁰⁾; oxalyl dichloride; ethanol; sodium hydride; sodium hydrogencarbonate; sodium carbonate; caesium carbonate; Dess-Martin periodane; triethylamine; N-ethyl-N,N-diisopropylamine; N,N-dimethyl-formamide; HATU; trifluoroacetic anhydride; potassium hydroxide; lithium hydroxide; In tetrahydrofuran; 1,4-dioxane; 1,2-dimethoxyethane; dichloromethane; water; N,N-dimethyl-formamide;