Potassium Iodide → 5-(5-Ethyl-2-methyl-6-oxo-1,6-dihydropyridin-3-yl)thiophene-2-carbaldehyde

HRID 1921309Notes

Reaction equation

HRID 1921309 reaction equation
[CH2:1]([C:3]1[CH:4]=[C:5]([C:12]2[S:16][C:15]([CH:17]=[O:18])=[CH:14][CH:13]=2)[C:6]([CH3:11])=[N:7][C:8]=1[O:9]C)[CH3:2].[I-].[K+].Cl[Si](C)(C)C>C(#N)C>[CH2:1]([C:3]1[C:8](=[O:9])[NH:7][C:6]([CH3:11])=[C:5]([C:12]2[S:16][C:15]([CH:17]=[O:18])=[CH:14][CH:13]=2)[CH:4]=1)[CH3:2]

Participants

5

Reactant 3

HCID 4875Potassium IodideHCID 6397ChlorotrimethylsilaneHCID 115217765-(5-Ethyl-6-methoxy-2-methylpyridin-3-yl)thiophene-2-carbaldehyde

Product 1

HCID 588085435-(5-Ethyl-2-methyl-6-oxo-1,6-dihydropyridin-3-yl)thiophene-2-carbaldehydeYield 167.3%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Conditions

Temperature
60 °C

Procedure

To a mixture of 5-(5-ethyl-6-methoxy-2-methylpyridin-3-yl)thiophene-2-carbaldehyde (0.7 g, 2.9 mmol) prepared in accordance with the procedures of Step 2 as described above, potassium iodide (1.43 g, 8.6 mmol) and acetonitrile (15 mL) is added chlorotrimethylsilane (1.1 mL, 8.6 mmol) at room temperature then the reaction is heated at 60° C. for 0.5 hr. Solid product begins to form so more solvent is added to facilitate stirring. The solids are collected by filtration, washed with water, with ether and dried to afford 5-(5-ethyl-2-methyl-6-oxo-1,6-dihydropyridin-3-yl)thiophene-2-carbaldehyde (1.2 g, 61% yield). MS: m/e=248 (M+H).

Workup

  1. customprepared in accordance with the procedures of Step 2
  2. customto form so more solvent
  3. additionis added
  4. filtrationThe solids are collected by filtration
  5. washwashed with water, with ether
  6. customdried

Sources & evidence

ORD record
ord-48245b33302c4981af23248b9263243b
Source dataset
uspto-grants-2012_05
Patent number
US08173682B2

Reaction notes

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