(Z)-6-benzyl-5,7-dihydro-5-(phenylmethylene)-6H-pyrrolo[3,4-b]pyridin-7-one

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Chemical Name:(Z)-6-benzyl-5,7-dihydro-5-(phenylmethylene)-6H-pyrrolo[3,4-b]pyridin-7-one
CAS No.:1338379-20-6
Molecular Formula:C₂₁H₁₆N₂O
Molecular Weight:312.371
Hs Code.:

Synonyms:(Z)-6-benzyl-5,7-dihydro-5-(phenylmethylene)-6H-pyrrolo[3,4-b]pyridin-7-one

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Chemical Property of (Z)-6-benzyl-5,7-dihydro-5-(phenylmethylene)-6H-pyrrolo[3,4-b]pyridin-7-one

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Technology Process of (Z)-6-benzyl-5,7-dihydro-5-(phenylmethylene)-6H-pyrrolo[3,4-b]pyridin-7-one

There total 3 articles about (Z)-6-benzyl-5,7-dihydro-5-(phenylmethylene)-6H-pyrrolo[3,4-b]pyridin-7-one 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:

: 1338379-17-1
N-benzyl-3-bromo-2-pyridinecarboxamide

: 536-74-3
phenylacetylene

: 1338379-20-6
(Z)-6-benzyl-5,7-dihydro-5-(phenylmethylene)-6H-pyrrolo[3,4-b]pyridin-7-one

: (E)-6-benzyl-5,7-dihydro-5-(phenylmethylene)-6H-pyrrolo[3,4-b]pyridin-7-one

Guidance literature:: With dichloro bis(acetonitrile) palladium(II); 2,2'-bis-(diphenylphosphino)-1,1'-binaphthyl; 1,8-diazabicyclo[5.4.0]undec-7-ene; In N,N-dimethyl-formamide; at 120 ℃; for 0.5h; optical yield given as %de; stereoselective reaction; Inert atmosphere; Microwave irradiation;
DOI:10.1016/j.tetlet.2011.08.070

Reference yield:

: 1049093-85-7
3-bromopicolinoyl chloride

: 1338379-20-6
(Z)-6-benzyl-5,7-dihydro-5-(phenylmethylene)-6H-pyrrolo[3,4-b]pyridin-7-one

: (E)-6-benzyl-5,7-dihydro-5-(phenylmethylene)-6H-pyrrolo[3,4-b]pyridin-7-one

Guidance literature:: Multi-step reaction with 2 steps

1: triethylamine / dichloromethane / 1 h / Inert atmosphere

2: dichloro bis(acetonitrile) palladium(II); 2,2'-bis-(diphenylphosphino)-1,1'-binaphthyl; 1,8-diazabicyclo[5.4.0]undec-7-ene / N,N-dimethyl-formamide / 0.5 h / 120 °C / Inert atmosphere; Microwave irradiation

With dichloro bis(acetonitrile) palladium(II); 2,2'-bis-(diphenylphosphino)-1,1'-binaphthyl; 1,8-diazabicyclo[5.4.0]undec-7-ene; triethylamine; In dichloromethane; N,N-dimethyl-formamide; 2: Sonogashira coupling/5-exo-dig cycloisomerization domino reaction;
DOI:10.1016/j.tetlet.2011.08.070

Reference yield:

: 30683-23-9
3-bromopicolinic acid

: 1338379-20-6
(Z)-6-benzyl-5,7-dihydro-5-(phenylmethylene)-6H-pyrrolo[3,4-b]pyridin-7-one

: (E)-6-benzyl-5,7-dihydro-5-(phenylmethylene)-6H-pyrrolo[3,4-b]pyridin-7-one

Guidance literature:: Multi-step reaction with 3 steps

1: oxalyl dichloride; N,N-dimethyl-formamide / benzene / 0.5 h / Inert atmosphere

2: triethylamine / dichloromethane / 1 h / Inert atmosphere

3: dichloro bis(acetonitrile) palladium(II); 2,2'-bis-(diphenylphosphino)-1,1'-binaphthyl; 1,8-diazabicyclo[5.4.0]undec-7-ene / N,N-dimethyl-formamide / 0.5 h / 120 °C / Inert atmosphere; Microwave irradiation

With dichloro bis(acetonitrile) palladium(II); oxalyl dichloride; 2,2'-bis-(diphenylphosphino)-1,1'-binaphthyl; 1,8-diazabicyclo[5.4.0]undec-7-ene; triethylamine; N,N-dimethyl-formamide; In dichloromethane; N,N-dimethyl-formamide; benzene; 3: Sonogashira coupling/5-exo-dig cycloisomerization domino reaction;
DOI:10.1016/j.tetlet.2011.08.070