N-Iodosuccinimide → HCID 67430914, compound

HRID 2036652Notes

Reaction equation

HRID 2036652 reaction equation
[CH3:1][O:2][C:3]([C:5]1[N:10]2[CH:11]=[C:12]([C@@H:14]([NH:16][C:17]([O:19][CH2:20][C:21]3[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=3)=[O:18])[CH3:15])[N:13]=[C:9]2[CH:8]=[CH:7][CH:6]=1)=[O:4].[I:27]N1C(=O)CCC1=O>C(#N)C.O>[CH2:20]([O:19][C:17]([NH:16][C@H:14]([C:12]1[N:13]=[C:9]2[CH:8]=[CH:7][CH:6]=[C:5]([C:3]([O:2][CH3:1])=[O:4])[N:10]2[C:11]=1[I:27])[CH3:15])=[O:18])[C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1

Participants

5

Reactant 2

HCID 120273N-IodosuccinimideHCID 67431045HCID 67431045, compound

Product 1

HCID 67430914HCID 67430914, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6342AcetonitrileSolvent

Conditions

Temperature
25 °C

Procedure

To a solution of (S)-methyl-2-(1-(((benzyloxy)carbonyl)amino)ethyl)imidazo[1,2-a]pyridine-5-carboxylate (5.5 g, 7.93 mmol) in acetonitrile (50 mL) was added N-iodosuccinimide (2.3 g, 10.3 mmol) at 25° C. The reaction mixture was stirred at 25° C. overnight. After completion of the reaction, the mixture was diluted with water and extracted with EtOAc. The organic layer was washed with satd. sodium bicarbonate solution, dried over sodium sulfate, filtered and concentrated in vacuo. The crude product was purified by column chromatography using silica gel (100-200 mesh) and 0-50% EtOAc in hexane to provide (S)-methyl 2-(1-(((benzyloxy)carbonyl)amino)ethyl)-3-iodoimidazo[1,2-a]pyridine-5-carboxylate: 1H NMR (CDCl3, 400 MHz) δ 1.547 (d, J=6.8 Hz, 3H), 4.048 (s, 3H), 5.067-5.200 (m, 3H), 5.805 (d, J=7.2 Hz, 1H), 7.229-7.260 (m, 2H), 7.292-7.350 (m, 5H), 7.675-7.708 (m, 1H); LC-MS (ESI) m/z 479.9 [M+H]+.

Workup

  1. customAfter completion of the reaction
  2. extractionextracted with EtOAc
  3. washThe organic layer was washed with satd
  4. dry with materialsodium bicarbonate solution, dried over sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. customThe crude product was purified by column chromatography

Sources & evidence

ORD record
ord-34d6515390a244c483438a2fe27908de
Source dataset
uspto-grants-2013_11
Patent number
US08575183B2

Reaction notes

Loading…