Carbon Tetrachloride → 3-(2-Chloro-ethoxymethyl)-3H-imidazo[4,5-b]pyridine

HRID 2112389Notes

Reaction equation

HRID 2112389 reaction equation
[N:1]1[C:9]2[C:4](=[N:5][CH:6]=[CH:7][CH:8]=2)[N:3]([CH2:10][O:11][CH2:12][CH2:13]O)[CH:2]=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C(Cl)(Cl)(Cl)[Cl:35]>N1C=CC=CC=1>[Cl:35][CH2:13][CH2:12][O:11][CH2:10][N:3]1[C:4]2=[N:5][CH:6]=[CH:7][CH:8]=[C:9]2[N:1]=[CH:2]1

Participants

5

Reactant 3

HCID 5943Carbon TetrachlorideHCID 11776TriphenylphosphineHCID 144640472-(3H-imidazo[4,5-b]pyridin-3-ylmethoxy)-ethanol

Product 1

HCID 688820923-(2-Chloro-ethoxymethyl)-3H-imidazo[4,5-b]pyridineYield 101.5%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

To a suspension of 0.63 g (3.26 mmol) 2-(3H-imidazo[4,5-b]pyridin-3-ylmethoxy)-ethanol and 1.71 g (6.52 mmol) triphenylphosphine in 10 ml pyridine kept under argon were added dropwise over 10 min. 0.32 ml (3.32 mmol) CCl4. The suspension was stirred at room temperature for 18 hours and concentrated in vacuo. The crude product was purified by flash chromatography (silica gel, gradient DCM→DCM/MeOH 9/1) and triturated with diethylether to afford 0.7 g of a brownish solid. MS(ISP): 212.1 [MH]+.

Workup

  1. additionwere added dropwise over 10 min
  2. concentrationconcentrated in vacuo
  3. customThe crude product was purified by flash chromatography (silica gel, gradient DCM→DCM/MeOH 9/1)
  4. customtriturated with diethylether

Sources & evidence

ORD record
ord-f78d742847754fc2a08c947b655ec0e0
Source dataset
uspto-grants-2009_04
Patent number
US07524823B2

Reaction notes

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