169749-88-6

Basic information

• Product Name: 2-(4-chloro-5-fluoro-3-methyl-2-pyridinyl)-2-cyclopropylacetaldehyde
• CAS NO: 169749-88-6
• Molecular Weight: 227.666
• Mol File: 169749-88-6.mol
• Article Data: 4

Chemical Properties

• CAS DataBase Reference: 2-(4-chloro-5-fluoro-3-methyl-2-pyridinyl)-2-cyclopropylacetaldehyde(CAS DataBase Reference)
• NIST Chemistry Reference: 2-(4-chloro-5-fluoro-3-methyl-2-pyridinyl)-2-cyclopropylacetaldehyde(169749-88-6)
• EPA Substance Registry System: 2-(4-chloro-5-fluoro-3-methyl-2-pyridinyl)-2-cyclopropylacetaldehyde(169749-88-6)

Safety Data

• Hazardous Substances Data: 169749-88-6(Hazardous Substances Data)

Upstream product

• 851386-40-8 4-chloro-2,5-difluoropyridine 
• 84476-99-3 2,5-difluoropyridine 
• 438238-05-2 2-(4-hydroxy-5-fluoro-3-methyl-2-pyridinyl)cyclopropaneacetonitrile 
• 169749-81-9 4-tert-butoxy-3-chloro-2,5,6-trifluoropyridine 
• 169749-82-0 4-t-Butoxy-2,3,6-trifluoropyridine 
• 1735-84-8 3-chloro-2,4,5,6-tetrafluoropyridine 
• 169750-50-9 2-(4-chloro-5-fluoro-3-methyl-2-pyridinyl)-2-cyclopropylethanol 
• 6542-60-5 2-cyclopropylacetonitrile 
• 169749-87-5 2-(4-chloro-5-fluoro-3-methyl-2-pyridinyl)-2-cyclopropylacetic acid,ethyl ester 
• 169749-85-3 2-(4-tert-butoxy-5-fluoro-3-methyl-2-pyridinyl)-2-cyclopropylacetonitrile 
• 169749-86-4 2-(4-chloro-5-fluoro-3-methylpyridin-2-yl)-2-cyclopropylacetonitrile 
• 169749-83-1 4-t-Butoxy-2,3,6-trifluoro-5-methylpyridine 
• 169749-84-2 4-t-butoxy-3-methyl-2,5-difluoropyridine 

Downstream Products

• 169749-89-7 8-chloro-1-cyclopropyl-7-fluoro-9-methyl-4-oxo-4H-quinolizine-3-carboxylic acid ethyl ester 
• 1027896-00-9 8-[(2-Benzyloxycarbonylamino-ethyl)-methyl-amino]-1-cyclopropyl-7-fluoro-9-methyl-4-oxo-4H-quinolizine-3-carboxylic acid 
• 1026247-25-5 8-[(2-Benzyloxycarbonylamino-ethyl)-methyl-amino]-1-cyclopropyl-7-fluoro-9-methyl-4-oxo-4H-quinolizine-3-carboxylic acid ethyl ester 
• 162763-53-3 (S)-8-(3-amino-1-pyrrolidinyl)-1-cyclopropyl-7-fluoro-9-methyl-4-oxo-4H-quinolizine-3-carboxylic acid hydrochloride 
• 1026729-95-2 8-((3aS,6aS)-1-Benzyloxycarbonyl-hexahydro-pyrrolo[3,4-b]pyrrol-5-yl)-1-cyclopropyl-7-fluoro-9-methyl-4-oxo-4H-quinolizine-3-carboxylic acid 
• 1026011-56-2 8-((3aR,6aR)-1-Benzyloxycarbonyl-hexahydro-pyrrolo[3,4-b]pyrrol-5-yl)-1-cyclopropyl-7-fluoro-9-methyl-4-oxo-4H-quinolizine-3-carboxylic acid ethyl ester 
• 162763-53-3 A-86504.1 
• 162763-53-3 A-87092.1 

Relevant articles and documents

8-chloro-1-cyclopropyl-7-fluorine-9-methyl-4-oxygen-4-hydrogen-quinolizine-3-carboxylic ester and preparation method thereof

The invention provides a preparation method of 8-chloro-1-cyclopropyl-7-fluorine-9-methyl-4-oxygen-4-hydrogen-quinolizine-3-carboxylic ester. The preparation method comprises the following steps: step one, enabling 2, 5-difluoropyridine and chlorine supply compound to react in a non-protonic solvent, and obtaining 4-chloro-2, 5-difluoropyridine; step two, enabling 4-chloro-2, 5-difluoropyridine and methyl donor to react in a non-protonic solvent, and obtaining 4-chloro-2, 5-difluoro-3-methylpyridine; step three, enabling 4-chloro-2, 5-difluoro-3-methylpyridine and cyclopropyl acetonitrile to react under the effect of strong base, and obtaining 2-(4-chloro-5-fluorine-3-methylpyridine-2-base)-2-cyclopropylacetonitrile; step four, preparing 2-(4-chloro-5-fluorine-3-methylpyridine-2-base)-2-cyclopropyl acetaldehyde; step five, enabling 2-(4-chloro-5-fluorine-3-methylpyridine-2-base)-2-cyclopropyl acetaldehyde and malonic ester to react, and obtaining 8-chloro-1-cyclopropyl-7-fluorine-9-methyl-4-oxygen-4-hydrogen-quinolizine-3-carboxylic ester. The method can reduce the synthesis steps of final products, and reduce the preparation cost.

Practical synthesis of 2-pyridone core: Ethyl 8-chloro-1-cyclopropyl-7- fluoro-9-methyl-4-oxo-4H-quinolizinone-3-carboxylate

A practical synthesis of the fluoropyridone core (2), an important intermediate to ABT-719 and other 2-pyridones, from the commercially available 3-chlorotetrafluoropyridine in 10 to 11 linear transformations with 10-26% overall yield is described.