Trifluoroacetic acid → HCID 67260294, compound

HRID 2368791Notes

Reaction equation

HRID 2368791 reaction equation
[F:1][C:2]1[CH:15]=[C:14]([F:16])[CH:13]=[CH:12][C:3]=1[CH2:4][C:5]1[CH:6]=[CH:7][C:8](=[O:11])[NH:9][CH:10]=1.C(O)(C(F)(F)F)=O.[I:24]N1C(=O)CCC1=O.[NH4+].[OH-]>C(O)(=O)C>[F:1][C:2]1[CH:15]=[C:14]([F:16])[CH:13]=[CH:12][C:3]=1[CH2:4][C:5]1[CH:6]=[C:7]([I:24])[C:8](=[O:11])[NH:9][CH:10]=1

Participants

6

Reactant 4

HCID 6422Trifluoroacetic acidHCID 14923Ammonium HydroxideHCID 120273N-IodosuccinimideHCID 67261265HCID 67261265, compound

Product 1

HCID 67260294HCID 67260294, compound

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

To a solution of 5-(2,4-difluorobenzyl)pyridin-2(1H)-one 3 (1.89 g, 8.5 mmol) in acetic acid (34 ml) was added TFA (2.2 ml), followed by N-iodosuccinimide (2.02 g, 8.5 mmol). The red homogeneous solution was allowed to stir overnight at room temperature, poured onto ice and neutralized with cone. NH4OH. The solid was collected by filtration, rinsed with water, treated with methanol/dichloromethane, dried over sodium sulfate, and evaporated. The resulting brown solid was purified by flash column chromatography on silica gel (hexanes:ethyl acetate, 50:50). Yield 2.57 g (87%). 1H NMR (CDCl3, 500 MHz): δ 13.20 (s, 1H), 7.98 (d, 1H, J=2.2 Hz), 7.26-6.81 (m, 4H), 3.70 (s, 2H). 13C NMR (CDCl3, 125 MHz): δ 162.5, 161.9, 160.5, 151.9, 133.5, 131.2, 121.8, 120.0, 111.6, 104.3, 91.6, 29.9.

Workup

  1. additionpoured onto ice and neutralized with cone
  2. filtrationThe solid was collected by filtration
  3. washrinsed with water
  4. additiontreated with methanol/dichloromethane
  5. dry with materialdried over sodium sulfate
  6. customevaporated
  7. customThe resulting brown solid was purified by flash column chromatography on silica gel (hexanes:ethyl acetate, 50:50)

Sources & evidence

ORD record
ord-a0a7455e1dfc49c29146b6233e64c387
Source dataset
uspto-grants-2014_04
Patent number
US08703801B2

Reaction notes

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