Water → HCID 67223465, compound

HRID 572257Notes

Reaction equation

Br[C:2]1[CH:7]=[CH:6][C:5]([C:8]2[N:9]([C:18]3[CH:23]=[CH:22][C:21]([O:24][CH3:25])=[CH:20][CH:19]=3)[CH:10]=[CH:11][C:12]=2[C:13]([O:15][CH2:16][CH3:17])=[O:14])=[C:4]([CH3:26])[CH:3]=1.[C:27]([Cu])#[N:28].[OH2:30]>CN(C=O)C>[C:27]([C:2]1[CH:7]=[CH:6][C:5]([C:8]2[N:9]([C:18]3[CH:23]=[CH:22][C:21]([O:24][CH3:25])=[CH:20][CH:19]=3)[CH:10]=[CH:11][C:12]=2[C:13]([O:15][CH2:16][CH3:17])=[O:14])=[C:4]([CH3:26])[CH:3]=1)(=[O:30])[NH2:28]

Participants

Conditions

Temperature: 180 °C

Procedure

To a mixture of ethyl 2-(4-bromo-2-methylphenyl)-1-(4-methoxyphenyl)-1H-pyrrole-3-carboxylate (1 g, 2.4 mmol) in DMF (50 mL) was added CuCN (0.43 g, 4.8 mmol), and the suspension solution was heated to 180° C. for 12 h. After being cooled down to room temperature, the reaction mixture was poured into water, and the mixture was extracted with ethyl acetate (50 mL×3). The combined organic layers were washed with brine, dried over Na2SO4, and concentrated under reduced pressure. The residue was purified on silica gel column chromatography (eluting with 50% ethyl acetate in petroleum ether) to give the title compound (600 mg, 66% yield) as a white solid.

Workup

temperatureAfter being cooled down to room temperature
extractionthe mixture was extracted with ethyl acetate (50 mL×3)
washThe combined organic layers were washed with brine
dry with materialdried over Na2SO4
concentrationconcentrated under reduced pressure
customThe residue was purified on silica gel column chromatography (eluting with 50% ethyl acetate in petroleum ether)

Sources & evidence

ORD record: ord-325f3b3fc2454f7fa88cd9c713639a29
Source dataset: uspto-grants-2015_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09029402B2

Reaction notes

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