N-Iodosuccinimide → HCID 22050117, compound

HRID 1831901Notes

Reaction equation

HRID 1831901 reaction equation
[CH2:1]([O:8][C:9]1[CH:14]=[CH:13][N:12]([CH2:15][C:16]2[CH:21]=[CH:20][CH:19]=[C:18]([F:22])[CH:17]=2)[C:11](=[O:23])[CH:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[I:24]N1C(=O)CCC1=O>C(#N)C>[CH2:1]([O:8][C:9]1[CH:14]=[CH:13][N:12]([CH2:15][C:16]2[CH:21]=[CH:20][CH:19]=[C:18]([F:22])[CH:17]=2)[C:11](=[O:23])[C:10]=1[I:24])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 120273N-IodosuccinimideHCID 220502224-benzyloxy-1-(3-fluorobenzyl)-1H-pyridin-2-one

Product 1

HCID 22050117HCID 22050117, compoundYield 90.6%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

Heated a reaction mixture of 4-(benzyloxy)-1-(3-fluorobenzyl)pyridin-2(1H)-one (4.83 g, 15.6 mmol) in anhydrous acetonitrile (55 mL) and N-iodosuccinimide (NIS, 3.86 g, 17.1 mmol) under nitrogen atmosphere at 650 C for 4 h. The reaction mixture was concentrated under reduced pressure and the residue was purified by flash chromatography (silica gel) using EtOAc/hexanes (1:1 v:v). The appropriate fractions were collected according to ES MS (M+H 436) and washed with Na2SO3 to remove the color impurities. The fractions were concentrated under reduced pressure and dried in vacuo to afford the desired product (6.15 g, 90%) as a light yellow solid.

Workup

  1. temperatureHeated
  2. concentrationThe reaction mixture was concentrated under reduced pressure
  3. customthe residue was purified by flash chromatography (silica gel)
  4. customThe appropriate fractions were collected
  5. washwashed with Na2SO3
  6. customto remove the color impurities
  7. concentrationThe fractions were concentrated under reduced pressure
  8. customdried in vacuo

Sources & evidence

ORD record
ord-ec539c599c0d411f8ec888a3ccce30f8
Source dataset
uspto-grants-2006_06
Patent number
US07067540B2

Reaction notes

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