Methane → Ethyl 5-(5-chloro-2-formylphenyl)-1,2-dimethyl-1H-pyrrole-3-carboxylate

HRID 518916Notes

Reaction equation

[CH3:1][N:2]1[CH:6]=[CH:5][C:4]([C:7]([O:9][CH2:10][CH3:11])=[O:8])=[C:3]1[CH3:12].Br[C:14]1[CH:21]=[C:20]([Cl:22])[CH:19]=[CH:18][C:15]=1[CH:16]=[O:17].C([O-])(=O)C.[K+].C>CN(C)C(=O)C.[Pd].ClCCl>[Cl:22][C:20]1[CH:19]=[CH:18][C:15]([CH:16]=[O:17])=[C:14]([C:6]2[N:2]([CH3:1])[C:3]([CH3:12])=[C:4]([C:7]([O:9][CH2:10][CH3:11])=[O:8])[CH:5]=2)[CH:21]=1

Participants

Conditions

Temperature: 130 °C

Procedure

To a solution of 10.5 g of the compound obtained in Step A (62.8 mmol) in 65 mL of N,N-dimethylacetamide there are successively added 15.2 g of 2-bromo-4-chlorobenzaldehyde (69 mmol), 12.3 g of potassium acetate (125.6 mmol) and then the batch is stirred under argon for 20 minutes. There are then added 2.2 g of palladium catalyst PdCl2(PPh3)2 (3.14 mmol). The reaction mixture is then heated at 130° C. overnight. The mixture is allowed to return to ambient temperature and it is then diluted with dichloromethane. Animal charcoal is added (30 g) and the batch is stirred at ambient temperature for 1 hour and then filtered. The organic phase is then washed with water, dried over magnesium sulphate and concentrated to dryness. The crude product thereby obtained is purified by chromatography over silica gel (petroleum ether/AcOEt gradient). The title product is obtained in the form of a solid.

Workup

customto return to ambient temperature
stirringthe batch is stirred at ambient temperature for 1 hour
filtrationfiltered
washThe organic phase is then washed with water
dry with materialdried over magnesium sulphate
concentrationconcentrated to dryness
customThe crude product thereby obtained
customis purified by chromatography over silica gel (petroleum ether/AcOEt gradient)

Sources & evidence

ORD record: ord-abd358a2af1f4e5b856f915e123dde85
Source dataset: uspto-grants-2015_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09115159B2

Reaction notes

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