Selectfluor → HCID 89826037, compound

HRID 2272987Notes

Reaction equation

HRID 2272987 reaction equation
[CH2:1]([O:3][C:4]([C:6]1[NH:7][CH:8]=[C:9]([F:11])[CH:10]=1)=[O:5])[CH3:2].[F:12][B-](F)(F)F.F[B-](F)(F)F.ClC[N+]12CC[N+](F)(CC1)CC2>C(#N)C>[CH2:1]([O:3][C:4]([C:6]1[NH:7][C:8]([F:12])=[C:9]([F:11])[CH:10]=1)=[O:5])[CH3:2]

Participants

4

Reactant 2

HCID 2724933SelectfluorHCID 72212396HCID 72212396, compound

Product 1

HCID 89826037HCID 89826037, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

4-Fluoro-1H-pyrrole-2-carboxylic acid ethyl ester (1.57 g, 10.0 mmol) is dissolved in acetonitrile (10 ml), 1-chloromethyl-4-fluoro-1,4-diazoniabicyclo[2.2.2]octane bis(tetrafluoroborate) (Selectfluor™, 3.54 g, 10.0 mmol) is added and the mixture is irradiated in a Biotage Initiator microwave synthesizer for 5 minutes at 70° C. The reaction mixture is allowed to cool to room temperature and partitioned between water and dichloromethane. The organic phase is dried over sodium sulfate and evaporated. The residue is chromatographed on a silica gel column with cyclohexane/ethyl acetate as eluent to afford 4,5-difluoro-1H-pyrrole-2-carboxylic acid ethyl ester as white solid; HPLC/MS 1.78 (C), [M+H] 176; 1H NMR (500 MHz, DMSO-d6) δ [ppm] 12.93 (s, 1H), 6.67 (d, J=4.5 Hz, 1H), 4.22 (q, J=7.1 Hz, 2H), 1.26 (t, J=7.1 Hz, 3H).

Workup

  1. customthe mixture is irradiated in a Biotage Initiator microwave synthesizer for 5 minutes at 70° C
  2. custompartitioned between water and dichloromethane
  3. dry with materialThe organic phase is dried over sodium sulfate
  4. customevaporated
  5. customThe residue is chromatographed on a silica gel column with cyclohexane/ethyl acetate as eluent

Sources & evidence

ORD record
ord-e517942e5e124086ba7934bd58ad5611
Source dataset
uspto-grants-2015_09
Patent number
US09120805B2

Reaction notes

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