Potassium ethanethioate → thioacetic acid, S-[2-(3H-imidazo[4,5-b]pyridin-3-ylmethoxy)-ethyl] ester

HRID 2112390Notes

Reaction equation

HRID 2112390 reaction equation
Cl[CH2:2][CH2:3][O:4][CH2:5][N:6]1[C:10]2=[N:11][CH:12]=[CH:13][CH:14]=[C:9]2[N:8]=[CH:7]1.[C:15]([O-:18])(=[S:17])[CH3:16].[K+]>CC(C)=O>[C:15]([S:17][CH2:2][CH2:3][O:4][CH2:5][N:6]1[C:10]2=[N:11][CH:12]=[CH:13][CH:14]=[C:9]2[N:8]=[CH:7]1)(=[O:18])[CH3:16]

Participants

4

Reactant 2

HCID 23670855Potassium ethanethioateHCID 688820923-(2-Chloro-ethoxymethyl)-3H-imidazo[4,5-b]pyridine

Product 1

HCID 86609191thioacetic acid, S-[2-(3H-imidazo[4,5-b]pyridin-3-ylmethoxy)-ethyl] esterYield 46%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

A suspension of 0.7 g (3.3 mmol) 3-(2-Chloro-ethoxymethyl)-3H-imidazo[4,5-b]pyridine and 378 mg (3.3 mmol) potassium thioacetate in 15 ml acetone was heated to reflux for 12 hours. The orange suspension was concentrated in vacuo. The crude product was purified by flash chromatography (silica gel, gradient of 0 to 10% methanol in DCM) to afford 380 mg (46%) of the desired product MS(ISP): 252.1 [MH]+; 1H-NMR (CDCl3): 2.28 (s, 3H), 3.05 (t, 2H), 3.69 (t, 2H), 5.72 (s, 2H), 7.27 (m, 1H), 8.09 (dd, 1H), 8.20 (s, 1H), 8.43 (dd, 1H).

Workup

  1. temperaturewas heated
  2. temperatureto reflux for 12 hours
  3. concentrationThe orange suspension was concentrated in vacuo
  4. customThe crude product was purified by flash chromatography (silica gel, gradient of 0 to 10% methanol in DCM)

Sources & evidence

ORD record
ord-5effab17d6344119a2aa80777ee77f73
Source dataset
uspto-grants-2009_04
Patent number
US07524823B2

Reaction notes

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