Water → Ethyl 4-cyano-5-fluoro-3-iodo-1-methylpyrrole-2-carboxylate

HRID 1865053Notes

Reaction equation

[CH2:1]([O:3][C:4]([C:6]1[N:7]([CH3:14])[CH:8]=[C:9]([C:12]#[N:13])[C:10]=1[I:11])=[O:5])[CH3:2].[B-](F)(F)(F)[F:16].[B-](F)(F)(F)F.C1[N+]2(CCl)CC[N+](F)(CC2)C1.O.C(Cl)Cl>C(#N)C>[C:12]([C:9]1[C:10]([I:11])=[C:6]([C:4]([O:3][CH2:1][CH3:2])=[O:5])[N:7]([CH3:14])[C:8]=1[F:16])#[N:13]

Participants

Conditions

Temperature: 80 °C

Procedure

Dissolve 4-cyano-3-iodo-1-methyl-1H-pyrrole-2-carboxylic acid ethyl ester (2.69 mmol, prepared in preparation 34) and SELECTFLUOR® (4.04 mmol, 1-chloromethyl-4-fluoro-1,4-diazoniabicyclo[2.2.2]octane bis-(tetrafluoroborate)) in acetonitrile (27 mL). Heat the mixture at 80° C. for 16 h. Add H2O (30 mL) and methylene chloride (30 mL) into the reaction mixture. Extract with methylene chloride (3×30 mL). Combine the organic layers, dry over magnesium sulfate, filter, and concentrate under reduced pressure. Purify the residue by flash chromatography to provide the title compound. Mass spectrum (m/e): 318.9 (M−1). Rf=0.5 (50% Et2O in hexanes).

Workup

extractionExtract with methylene chloride (3×30 mL)
dry with materialCombine the organic layers, dry over magnesium sulfate
filtrationfilter
concentrationconcentrate under reduced pressure
customPurify the residue by flash chromatography

Sources & evidence

ORD record: ord-2ca4518cd5e44a02b92361d740909bf7
Source dataset: uspto-grants-2009_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07625932B2

Reaction notes

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