Thionyl Chloride → 2-(2-Chloroethyl)imidazo[1,2-A]pyridine

HRID 920916Notes

Reaction equation

HRID 920916 reaction equation
[N:1]1[C:2]([CH2:10][CH2:11]O)=[CH:3][N:4]2[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=12.O=S(Cl)[Cl:15]>C(Cl)Cl>[Cl:15][CH2:11][CH2:10][C:2]1[N:1]=[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][N:4]2[CH:3]=1

Participants

4

Reactant 2

HCID 24386Thionyl ChlorideHCID 104872012-(Imidazo[1,2-a]pyridin-2-yl)ethanol

Product 1

HCID 157181812-(2-Chloroethyl)imidazo[1,2-A]pyridineYield 70%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A mixture of 2-(imidazo[1,2-a]pyridin-2-yl)ethanol (400 mg, 2.466 mmol) from Example a4) and SOCl2 (2 mL, 27.4 mmol) in DCM (10 mL) was stirred at room temperature for 2 days. The mixture was concentrated in vacuo. The residue was diluted with EtOAc (3×100 mL) and washed with saturated NaHCO3 solution (6 mL×4) and brine (6 mL). The organic layer was dried over Na2SO4, filtered and concentrated in vacuo. The residue was purified by Pre-TLC (PE/EA=1/1, v/v) to give the title compound as an oil (300 mg, yield 70%).

Workup

  1. concentrationThe mixture was concentrated in vacuo
  2. additionThe residue was diluted with EtOAc (3×100 mL)
  3. washwashed with saturated NaHCO3 solution (6 mL×4) and brine (6 mL)
  4. dry with materialThe organic layer was dried over Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. customThe residue was purified by Pre-TLC (PE/EA=1/1

Sources & evidence

ORD record
ord-8e34a3b546134624858c49d0d5cf8951
Source dataset
uspto-grants-2016_03
Patent number
US09273068B2

Reaction notes

Loading…