Hydrochloric Acid → HCID 19419294, compound

HRID 2396539Notes

Reaction equation

C([Li])CCC.Br[C:7]1[O:11][C:10]([C:12]2[NH:13][C:14]([C:19]([F:22])([F:21])[F:20])=[CH:15][C:16]=2[C:17]#[N:18])=[CH:9][CH:8]=1.CN(C)[CH:25]=[O:26].Cl>O1CCCC1.CCCCCC.C(OCC)(=O)C>[CH:25]([C:7]1[O:11][C:10]([C:12]2[NH:13][C:14]([C:19]([F:22])([F:21])[F:20])=[CH:15][C:16]=2[C:17]#[N:18])=[CH:9][CH:8]=1)=[O:26]

Participants

Conditions

Temperature: -78 °C

Procedure

Butyllithium (3.45 mL, 7.78 mmol) is added dropwise to a solution of 2-(5-bromo-2-furyl)-5-(trifluoromethyl) pyrrole-3-carbonitrile (1.13 g, 3.70 mmol) in tetrahydrofuran at -78° C. The reation mixture is stirred at -78° C. for 30 minutes, warmed to room temperature, treated with N,N-dimethylformamide (1.35 g, 18.5 mmol), poured into one molar hydrochloric acid and extracted with ether and ethyl acetate. The combined organic extracts are washed sequentially with water and brine, dried over Na2SO4 and concentrated in vacuo to obtain an orange solid. Flash chromatography of the solid using silica gel and 20% to 50% ethyl acetate in hexane solutions give an orange solid which is recrystallized from ethyl acetate to obtain the title product as orange crystals (0.66 g, 70%, mp 224°-225° C.).

Workup

temperaturewarmed to room temperature
extractionextracted with ether and ethyl acetate
washThe combined organic extracts are washed sequentially with water and brine
dry with materialdried over Na2SO4
concentrationconcentrated in vacuo
customto obtain an orange solid
customgive an orange solid which
customis recrystallized from ethyl acetate

Sources & evidence

ORD record: ord-d7f0d1896b5040ab93f542f6646746bb
Source dataset: uspto-grants-1996_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05492925

Reaction notes

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