Pyrrole-2-carboxylic acid, 4-acetyl-3,5-dimethyl-, ethyl ester → HCID 68561273, compound

HRID 272630Notes

Reaction equation

[CH2:1]([O:3][C:4]([C:6]1[NH:7][C:8]([CH3:15])=[C:9]([C:12](=[O:14])[CH3:13])[C:10]=1[CH3:11])=[O:5])[CH3:2].CC(O[CH:21](N(C)C)[N:22]([CH3:24])[CH3:23])(C)C>C1COCC1>[CH2:1]([O:3][C:4]([C:6]1[NH:7][C:8]([CH3:15])=[C:9]([C:12](=[O:14])[CH:13]=[CH:21][N:22]([CH3:24])[CH3:23])[C:10]=1[CH3:11])=[O:5])[CH3:2]

Participants

Conditions

Temperature: 50 °C

Procedure

In a dry flask containing THF (15 mL) was added 4-acetyl-3,5-dimethyl-1H-pyrrole-2-carboxylic acid ethyl ester (2.0 g, 9.3 mmol) then Bredereck's reagent (5 mL). The reaction was stirred at 50° C. for 20 hours. The resulting precipitate formed during the reaction was removed by filtration and washed with hexanes. The enaminone was recovered as a yellow solid (2.2 g), HPLC Rt=4.0 minutes; FIA, ES+=265.1

Workup

customThe resulting precipitate formed during the reaction
customwas removed by filtration
washwashed with hexanes
customThe enaminone was recovered as a yellow solid (2.2 g), HPLC Rt=4.0 minutes

Sources & evidence

ORD record: ord-593cb93a021344148565231a66b138f0
Source dataset: uspto-grants-2008_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07456190B2

Reaction notes

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