N-Iodosuccinimide → HCID 118195270, compound

HRID 1048688Notes

Reaction equation

HRID 1048688 reaction equation
[N:1]1[C:2]([CH2:10][O:11][CH2:12][C:13]([O:15][CH2:16][CH3:17])=[O:14])=[CH:3][N:4]2[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=12.[I:18]N1C(=O)CCC1=O>C(#N)C>[I:18][C:3]1[N:4]2[CH:9]=[CH:8][CH:7]=[CH:6][C:5]2=[N:1][C:2]=1[CH2:10][O:11][CH2:12][C:13]([O:15][CH2:16][CH3:17])=[O:14]

Participants

4

Reactant 2

HCID 120273N-IodosuccinimideHCID 118195252HCID 118195252, compound

Product 1

HCID 118195270HCID 118195270, compoundYield 67.2%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

0.45 g (1.921 mmol) of ethyl 2-(imidazo[1,2-a]pyridin-2-ylmethoxy)acetate were solubilised in 6 ml of acetonitrile with magnetic stirring, to this solution were added 0.475 g (2.113 mmol) of N-iodosuccinimide. The mixture was stirred at r.t. for 16 h. A solid was removed by filtration and the obtained filtrate was concentrated in vacuo. The residue was triturated with 10 ml of diisopropyl ether and a precipitate was isolated by filtration. 0.465 g (yield=67%) ethyl 2-((3-iodoimidazo[1,2-a]pyridin-2-yl)methoxy)acetate were obtained as a yellow solid. LC-MS: m/z=361 (MH+); UV purity at 254 nm=75%. 1H NMR (300 MHz, DMSO) δ 8.34 (d, J=6.9 Hz, 1H), 7.59 (d, J=8.1 Hz, 1H), 7.47-7.28 (m, 1H), 7.07 (d, J=5.7 Hz, 1H), 4.67 (s, 2H), 4.14 (t, J=10.7 Hz, 4H), 1.22 (d, J=1.9 Hz, 3H)

Workup

  1. customA solid was removed by filtration
  2. concentrationthe obtained filtrate was concentrated in vacuo
  3. customThe residue was triturated with 10 ml of diisopropyl ether
  4. customa precipitate was isolated by filtration

Sources & evidence

ORD record
ord-47002306bab44f7d9d903b6422fd5e8b
Source dataset
uspto-grants-2016_07
Patent number
US09381191B2

Reaction notes

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