Ethylene Glycol → 2-(5-(1,3-Dioxolan-2-yl)pyridin-2-yl)-7-chlorothieno[3,2-b]pyridine

HRID 84380Notes

Reaction equation

HRID 84380 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][N:5]=[C:4]2[CH:8]=[C:9]([C:11]3[CH:18]=[CH:17][C:14]([CH:15]=[O:16])=[CH:13][N:12]=3)[S:10][C:3]=12.[CH2:19](O)[CH2:20][OH:21].[C@@]12(CS(O)(=O)=O)C(C)(C)C(CC1)CC2=O>C1(C)C=CC=CC=1>[O:16]1[CH2:19][CH2:20][O:21][CH:15]1[C:14]1[CH:17]=[CH:18][C:11]([C:9]2[S:10][C:3]3[C:4](=[N:5][CH:6]=[CH:7][C:2]=3[Cl:1])[CH:8]=2)=[N:12][CH:13]=1

Participants

5

Reactant 3

HCID 174Ethylene GlycolHCID 131278(R)-camphorsulfonic acidHCID 579196526-(7-Chlorothieno[3,2-b]pyridin-2-yl)nicotinaldehyde

Product 1

HCID 579195542-(5-(1,3-Dioxolan-2-yl)pyridin-2-yl)-7-chlorothieno[3,2-b]pyridineYield 89%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A suspension of 136 (2.69 g, 9.79 mmol), ethylene glycol (2.184 mL, 39.2 mmol), and (1R)-(−)-10-camphorsulfonic acid (0.227 g, 0.979 mmol) in toluene (150 mL) was heated to reflux with a Dean-Stark trap. After 3 h, the mixture was cooled down and filtered through celite (while still warm). The filtrate was washed with water, NaHCO3 (aq., sat.), NaOH (aq) and brine. The solution was then dried over MgSO4 and concentrated to afford compound 137 (2.77 g, 89% yield) as an off-white solid. MS (m/z): 319.1 (M+H).

Workup

  1. temperaturewas heated
  2. temperatureto reflux with a Dean-Stark trap
  3. temperaturethe mixture was cooled down
  4. filtrationfiltered through celite (
  5. temperaturewhile still warm)
  6. washThe filtrate was washed with water, NaHCO3 (aq., sat.), NaOH (aq) and brine
  7. dry with materialThe solution was then dried over MgSO4
  8. concentrationconcentrated

Sources & evidence

ORD record
ord-56a6bf9539c84dc49769b4bebeb634d4
Source dataset
uspto-grants-2014_09
Patent number
US08846927B2

Reaction notes

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