Water → HCID 118195178, compound

HRID 1048705Notes

Reaction equation

HRID 1048705 reaction equation
[N:1]1[C:2]([CH2:10][N:11]([CH3:17])[CH2:12][C:13]([O:15][CH3:16])=[O:14])=[CH:3][N:4]2[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=12.[I:18]N1C(=O)CCC1=O.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][N:11]([CH3:17])[CH2:12][C:13]([O:15][CH3:16])=[O:14]

Participants

5

Reactant 3

HCID 962WaterHCID 120273N-IodosuccinimideHCID 60670418HCID 60670418, compound

Product 1

HCID 118195178HCID 118195178, compoundYield 56.4%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

0.107 g (0.459 mmol) of methyl 2-((imidazo[1,2-a]pyridin-2-ylmethyl)(methyl)amino)acetate were dissolved in 4 ml of acetonitrile with magnetic stirring, to this solution were added 0.112 g (0.482 mmol) of N-iodosuccinimide. The mixture was stirred at r.t. for 16 h. The reaction mixture was treated with 10 ml of water and then extracted with 3×10 ml of ethyl acetate. The combined organic phases were washed with 20 ml of a saturated NaCl aqueous solution, and then dried on Na2SO4 which was then removed by filtration. The obtained filtrate was concentrated in vacuo. The crude residue was purified by flash chromatography on a silica gel cartridge (eluent: ethyl acetate 100%). 0.093 g (yield=46%) of methyl 2-(((3-iodoimidazo[1,2-a]pyridin-2-yl)methyl)(methyl)amino)acetate were obtained as a yellow oil. LC-MS: m/z=360 (MH+); UV purity at 254 nm=82%. 1H NMR (300 MHz, DMSO) δ 8.30 (d, J=6.8 Hz, 1H), 7.54 (d, J=9.0 Hz, 1H), 7.41-7.23 (m, 1H), 7.03 (t, J=6.7 Hz, 1H), 3.79 (s, 2H), 3.62 (s, 3H), 3.37 (s, 2H), 2.34 (s, 3H).

Workup

  1. extractionextracted with 3×10 ml of ethyl acetate
  2. washThe combined organic phases were washed with 20 ml of a saturated NaCl aqueous solution
  3. customdried on Na2SO4 which
  4. customwas then removed by filtration
  5. concentrationThe obtained filtrate was concentrated in vacuo
  6. customThe crude residue was purified by flash chromatography on a silica gel cartridge (eluent: ethyl acetate 100%)

Sources & evidence

ORD record
ord-535ab65d0c4e49ac9094b9ea888d6443
Source dataset
uspto-grants-2016_07
Patent number
US09381191B2

Reaction notes

Loading…