Cesium carbonate → 3-Chloro-5-(1H-imidazol-2-ylsulfanyl)-pyridine-4-carbaldehyde

HRID 1959563Notes

Reaction equation

HRID 1959563 reaction equation
Cl[C:2]1[CH:3]=[N:4][CH:5]=[C:6]([Cl:10])[C:7]=1[CH:8]=[O:9].[NH:11]1[CH:15]=[CH:14][N:13]=[C:12]1[SH:16].C([O-])([O-])=O.[Cs+].[Cs+]>C1COCC1>[Cl:10][C:6]1[CH:5]=[N:4][CH:3]=[C:2]([S:16][C:12]2[NH:11][CH:15]=[CH:14][N:13]=2)[C:7]=1[CH:8]=[O:9]

Participants

5

Reactant 3

HCID 10796Cesium carbonateHCID 27629883,5-Dichloro-4-pyridinecarboxaldehydeHCID 178527877HCID 178527877, compound

Product 1

HCID 866453563-Chloro-5-(1H-imidazol-2-ylsulfanyl)-pyridine-4-carbaldehyde

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A mixture of 3,5-dichloro-pyridine-4-carbaldehyde (600 mg, 3.41 mmol), 1H-imidazole-2-thiol (341 mg, 3.41 mmol) and Cs2CO3 (1.33 g, 4.09 mmol) in THF (10 mL) was stirred at RT for 8.5 h. The solvent was removed in vacuo and the residue was partitioned between EA (30 mL) and brine (30 mL). After extraction of the aqueous layer with EA (2×30 mL) the combined organic layers were dried over Na2SO4, filtered, and concentrated in vacuo. The resulting title compound was used for the next reaction without purification. MS (m/z): 240.0 [M+H+].

Workup

  1. customThe solvent was removed in vacuo
  2. customthe residue was partitioned between EA (30 mL) and brine (30 mL)
  3. extractionAfter extraction of the aqueous layer with EA (2×30 mL) the combined organic layers
  4. dry with materialwere dried over Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. customThe resulting title compound was used for the next reaction without purification

Sources & evidence

ORD record
ord-146570afac144cfc80ae0ae6c74269da
Source dataset
uspto-grants-2013_04
Patent number
US08410134B2

Reaction notes

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