N-Iodosuccinimide → HCID 22050830, compound

HRID 2243565Notes

Reaction equation

HRID 2243565 reaction equation
[I:1]N1C(=O)CCC1=O.[CH2:9]([N:16]1[CH:21]=[CH:20][C:19]([O:22][CH2:23][C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=2)=[CH:18][C:17]1=[O:30])[C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1.[Al].C(OCC)(=O)C.CCCCCC>C(#N)C>[CH2:9]([N:16]1[CH:21]=[CH:20][C:19]([O:22][CH2:23][C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=2)=[C:18]([I:1])[C:17]1=[O:30])[C:10]1[CH:11]=[CH:12][CH:13]=[CH:14][CH:15]=1

Participants

6

Reactant 4

HCID 120273N-IodosuccinimideHCID 5359268AluminumHCID 101930321-benzyl-4-(benzyloxy)pyridin-2(1H)-oneHCID 21226206Ethyl acetate hexane

Product 1

HCID 22050830HCID 22050830, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

In accordance with a method similar to that described in Bossharth, E.; Desbordes, P; Monteiro, N.; Balme, G. Org. Lett., 5, 2441-2444, 2003, N-Iodosuccinimide (1.390 g, 6.18 mmol) was added to a solution of 1-benzyl-4-benzyloxy-2-pyridone 2 (1.00 g, 3.43 mmol) in acetonitrile (69 mL). The mixture was covered with aluminum foil and stirred at room temperature for 20 h. The reaction mixture was concentrated to afford a crude orange oil. This oil was purified via column chromatography on silica gel (gradient elution with 0-50% ethyl acetate/hexane) to afford an orange solid. Trituration with 50% ethyl acetate/hexane afforded 1-benzyl-4-benzyloxy-3-iodo-2-pyridone 3 as an off-white solid. MS (MH+) 418.0; Calculated 417 for C19H16INO2.

Workup

  1. concentrationThe reaction mixture was concentrated
  2. customto afford a crude orange oil
  3. customThis oil was purified via column chromatography on silica gel (gradient elution with 0-50% ethyl acetate/hexane)
  4. customto afford an orange solid

Sources & evidence

ORD record
ord-cb827aa6be304360832027813fc04258
Source dataset
uspto-grants-2010_03
Patent number
US07674907B2

Reaction notes

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