Water → 4-cyano-3-(4-cyclopentyl-phenyl)-1-methyl-1H-pyrrole-2-carboxylic acid ethyl ester

HRID 1865073Notes

Reaction equation

[Br-].[CH:2]1([Zn+])[CH2:6][CH2:5][CH2:4][CH2:3]1.[CH2:8]([O:10][C:11]([C:13]1[N:14]([CH3:27])[CH:15]=[C:16]([C:25]#[N:26])[C:17]=1[C:18]1[CH:23]=[CH:22][C:21](Br)=[CH:20][CH:19]=1)=[O:12])[CH3:9].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.O>O1CCOCC1>[CH2:8]([O:10][C:11]([C:13]1[N:14]([CH3:27])[CH:15]=[C:16]([C:25]#[N:26])[C:17]=1[C:18]1[CH:23]=[CH:22][C:21]([CH:2]2[CH2:6][CH2:5][CH2:4][CH2:3]2)=[CH:20][CH:19]=1)=[O:12])[CH3:9]

Participants

Conditions

Temperature: 80 °C

Procedure

Add cyclopentylzinc bromide (0.5M, 7.2 mL, 3.6 mmol) to 3-(4-bromo-phenyl)-4-cyano-1-methyl-1H-pyrrole-2-carboxylic acid ethyl ester (0.50 g, 1.80 mmol, prepared in example E-3a or E-3b), tris(dibenzylideneacetone)palladium(0) (0.06 g, 0.07 mmol), and triphenylphosphine (0.07 g, 0.27 mmol) in dioxane and heat to 80° C. with stirring. After 18 hours, cool the reaction mixture, and pour into water. Extract the quenched reaction mixture with ethyl acetate. Combine the organic extracts, wash with water and brine, dry over anhydrous magnesium sulfate, filter, and concentrate under reduced pressure. Purify the residue by flash chromatography eluting with ethyl acetate:hexane to provide the title compound. Mass spectrum (m/e): 323.3 (M+1).

Workup

temperaturecool the reaction mixture
extractionExtract
customthe quenched reaction mixture with ethyl acetate
washwash with water and brine
dry with materialdry over anhydrous magnesium sulfate
filtrationfilter
concentrationconcentrate under reduced pressure
customPurify the residue by flash chromatography
washeluting with ethyl acetate

Sources & evidence

ORD record: ord-aa52e5fa583d4b1b92ecf4195cc1c8df
Source dataset: uspto-grants-2009_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07625932B2

Reaction notes

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