Trifluoroacetic acid → HCID 178517721, compound

HRID 2075218Notes

Reaction equation

HRID 2075218 reaction equation
[CH2:1]([C:8]1[CH:9]=[CH:10][C:11]([OH:14])=[N:12][CH:13]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(O)(C(F)(F)F)=O.[I:22]N1C(=O)CCC1=O.[NH4+].[OH-]>CC(O)=O>[CH2:1]([C:8]1[CH:9]=[C:10]([I:22])[C:11]([OH:14])=[N:12][CH:13]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

6

Reactant 4

HCID 6422Trifluoroacetic acidHCID 14923Ammonium HydroxideHCID 120273N-IodosuccinimideHCID 178515962HCID 178515962, compound

Product 1

HCID 178517721HCID 178517721, compound

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

To a yellow solution of 5-benzylpyridin-2-ol (1.10 g, 5.94 mmol) in 22 mL AcOH under Ar was added 1.5 mL TFA, followed by N-iodosuccinimide (1.34 g, 5.94 mmol). The red homogeneous solution was allowed to stir overnight, poured onto ice and neutralized with conc. NH4OH. The solids were collected by filtration, rinsed with water, treated with MeOH/DCM, dried over sodium sulfate, and evaporated. The resulting brown solid was purified by silica gel chromatography (ISCO, 80 g, 0-70% 90/10 DCM/MeOH in DCM) to give 5-benzyl-3-iodopyridin-2-ol as a yellow/brown solid. MS (ESI) m/z: Calculated: 311.0; Observed: 311.9 (M++1).

Workup

  1. filtrationThe solids were collected by filtration
  2. washrinsed with water
  3. additiontreated with MeOH/DCM
  4. dry with materialdried over sodium sulfate
  5. customevaporated
  6. customThe resulting brown solid was purified by silica gel chromatography (ISCO, 80 g, 0-70% 90/10 DCM/MeOH in DCM)

Sources & evidence

ORD record
ord-74f79c4a41ad4bfba621444c30003354
Source dataset
uspto-grants-2011_04
Patent number
US07919519B2

Reaction notes

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