N-Iodosuccinimide → HCID 12321880, compound

HRID 2252034Notes

Reaction equation

HRID 2252034 reaction equation
[C:1]1([C:7]2[N:8]=[C:9]3[CH:14]=[CH:13][CH:12]=[CH:11][N:10]3[CH:15]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[I:16]N1C(=O)CCC1=O>C(#N)C.CCOCC>[I:16][C:15]1[N:10]2[CH:11]=[CH:12][CH:13]=[CH:14][C:9]2=[N:8][C:7]=1[C:1]1[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

5

Reactant 2

HCID 120273N-IodosuccinimideHCID 2011362-phenylimidazo[1,2-a]pyridine

Product 1

HCID 12321880HCID 12321880, compoundYield 97%

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 6342AcetonitrileSolvent

Procedure

Treat a solution of 2-phenylimidazo[1,2-a]pyridine (50 mg, 0.257 mmol) in acetonitrile (1.25 mL) with N-iodosuccinimide (NIS) (69 mg, 0.309 mmol) at room temperature for 5 hours. Dilute the mixture with ether (10 mL), wash with a saturated aqueous solution of NaHCO3 (15 mL) and NaHSO3 (40%, 15 mL), dry (Na2SO4) and concentrate in vacuo. A yellow solid is obtained, 80 mg, 97% yield. MS(ES+): m/z=321.0 (M+H)+

Workup

  1. washwash with a saturated aqueous solution of NaHCO3 (15 mL) and NaHSO3 (40%, 15 mL)
  2. dry with materialdry (Na2SO4)
  3. concentrationconcentrate in vacuo
  4. customA yellow solid is obtained

Sources & evidence

ORD record
ord-b3b8c606929f47cda020c3b91d93c264
Source dataset
uspto-grants-2008_01
Patent number
US07320995B2

Reaction notes

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