N-Iodosuccinimide → HCID 71484324, compound

HRID 1048698Notes

Reaction equation

HRID 1048698 reaction equation
[Cl:1][CH2:2][C:3]1[N:4]=[C:5]2[CH:10]=[CH:9][CH:8]=[CH:7][N:6]2[CH:11]=1.[I:12]N1C(=O)CCC1=O>C(#N)C>[Cl:1][CH2:2][C:3]1[N:4]=[C:5]2[CH:10]=[CH:9][CH:8]=[CH:7][N:6]2[C:11]=1[I:12]

Participants

4

Reactant 2

HCID 120273N-IodosuccinimideHCID 9576142-Chloromethyl-imidazo(1,2-A)pyridine

Product 1

HCID 71484324HCID 71484324, compoundYield 96.4%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

5 g (30 mmol) of 2-(chloromethyl)imidazo[1,2-a]pyridine were solubilised in 60 ml of acetonitrile with magnetic stirring, 7.31 g (31.5 mmol) of N-iodosuccinimide were added and the mixture was stirred at r.t. for 15 min. The solid formed was isolated by filtration, washed with 30 ml of water and dried in a vacuum bell jar. 8.46 g (yield=95%) of 2-(chloromethyl)-3-iodoimidazo[1,2-a]pyridine were obtained as a white solid. LC-MS: m/z=293 (MH+); UV purity at 254 nm=99%. 1H NMR (300 MHz, DMSO) δ 8.31 (d, J=6.9 Hz, 1H), 7.58 (d, J=9.1 Hz, 1H), 7.46-7.29 (m, 1H), 7.07 (td, J=6.8, 1.0 Hz, 1H), 4.81 (s, 2H).

Workup

  1. additionwere added
  2. customThe solid formed
  3. customwas isolated by filtration
  4. washwashed with 30 ml of water
  5. customdried in a vacuum bell jar

Sources & evidence

ORD record
ord-e6339090121c43e08b00139ee7fb0028
Source dataset
uspto-grants-2016_07
Patent number
US09381191B2

Reaction notes

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