Potassium Carbonate → HCID 68512497, compound

HRID 1877281Notes

Reaction equation

[CH3:1][C:2]1[C:3]([C:7]([O:9][CH3:10])=[O:8])=[CH:4][NH:5][CH:6]=1.[F:11][C:12]([F:21])([F:20])[C:13]1[CH:14]=[C:15](I)[CH:16]=[CH:17][CH:18]=1.C(=O)([O-])[O-].[K+].[K+]>CN1CCCC1=O>[CH3:1][C:2]1[C:3]([C:7]([O:9][CH3:10])=[O:8])=[CH:4][N:5]([C:17]2[CH:16]=[CH:15][CH:14]=[C:13]([C:12]([F:21])([F:20])[F:11])[CH:18]=2)[CH:6]=1

Participants

Conditions

Temperature: 170 °C

Procedure

To a solution of methyl 4-methyl-1H-pyrrole-3-carboxylate (3.4 g) synthesized above in N-methyl-2-pyrrolidone (30 mL) were added 3-trifluoromethyliodobenzene (6.7 g), cuprous bromide (0.53 g) and potassium carbonate (4.4 g) at room temperature, and stirred for 1 hr with heating to 170° C. After cooling to room temperature, the reaction mixture was filtered through celite. Water was added to the filtrate and the mixture was extracted with diethyl ether. The extract was washed with brine, dried over magnesium sulfate, and concentrated under reduced pressure. The residue was purified by silica gel chromatography (ethyl acetate:hexane=1:4, volume ratio) to give the title compound (3.0 g, 42%) as a slightly yellow solid.

Workup

temperatureAfter cooling to room temperature
filtrationthe reaction mixture was filtered through celite
additionWater was added to the filtrate
extractionthe mixture was extracted with diethyl ether
washThe extract was washed with brine
dry with materialdried over magnesium sulfate
concentrationconcentrated under reduced pressure
customThe residue was purified by silica gel chromatography (ethyl acetate:hexane=1:4, volume ratio)

Sources & evidence

ORD record: ord-99b0c4c9fd23404e891d7b29a8d33423
Source dataset: uspto-grants-2012_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08309580B2

Reaction notes

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