Sodium Iodide → HCID 90031876, compound

HRID 1048687Notes

Reaction equation

HRID 1048687 reaction equation
Cl[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-].[Na+].[OH:14][CH2:15][C:16]([O:18]CC)=[O:17].[H-].[Na+].ICC1N=C2C=CC=CN2C=1>O1CCCC1>[N:4]1[C:3]([CH2:2][O:14][CH2:15][C:16]([OH:18])=[O:17])=[CH:11][N:6]2[CH:7]=[CH:8][CH:9]=[CH:10][C:5]=12

Participants

7

Reactant 5

HCID 5238Sodium IodideHCID 12184Ethyl GlycolateHCID 24758Sodium hydrideHCID 9576142-Chloromethyl-imidazo(1,2-A)pyridineHCID 64788548HCID 64788548, compound

Product 1

HCID 90031876HCID 90031876, compoundYield 69.1%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent3×

Conditions

Temperature
0 °C

Procedure

4.24 g (25.4 mmol) of 2-(chloromethyl)imidazo[1,2-a]pyridine were dissolved in 150 ml of tetrahydrofurane with magnetic stirring and then 4.2 g (28 mmol) of sodium iodide were added. The mixture was stirred at r.t. for 3 h. In another flask, 9.84 ml (101.8 mmol) of ethyl 2-hydroxyacetate were solubilized in 100 ml of tetrahydrofurane with magnetic stirring, and then the mixture was cooled to 0° C. and 4.072 g (101.8 mmol) of sodium hydride were added portionwise. The mixture was stirred 15 min at 0° C. and then the freshly prepared solution of 2-(iodomethyl)imidazo[1,2-a]pyridine in tetrahydrofurane was added drop wise within 15 min. The mixture was stirred at r.t. for 24 h before being filtered on silica (eluent: tetrahydrofurane 100%). The filtrate was concentrated in vacuo and directly purified by flash chromatography on a silica gel cartridge (eluent: dichloromethane/methanol gradient, from 100% to 70% of dichloromethane, v/v; and then washing the cartridge with 100% methanol). 3.62 g (yield=69%) of 2-(imidazo[1,2-a]pyridin-2-ylmethoxy)acetic acid were obtained as a beige solid. LC-MS: m/z=207 (MH+); UV purity at 254 nm=98%.

Workup

  1. stirringThe mixture was stirred at r.t. for 3 h
  2. stirringThe mixture was stirred 15 min at 0° C.
  3. stirringThe mixture was stirred at r.t. for 24 h
  4. filtrationbefore being filtered on silica (eluent: tetrahydrofurane 100%)
  5. concentrationThe filtrate was concentrated in vacuo
  6. customdirectly purified by flash chromatography on a silica gel cartridge (eluent
  7. washand then washing the cartridge with 100% methanol)

Sources & evidence

ORD record
ord-18d8b2d3c0524e88b36e6a33c9ab1f7d
Source dataset
uspto-grants-2016_07
Patent number
US09381191B2

Reaction notes

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