Methyl iodide → 2-(Methylthio)thiazolo[5,4-b]pyridine

HRID 707274

Reaction equation

HRID 707274 reaction equation
[N:1]1[C:9]2[C:4](=[N:5][CH:6]=[CH:7][CH:8]=2)[S:3][C:2]=1[SH:10].[C:11](=O)([O-])[O-].[K+].[K+].IC>C1COCC1.C(OCC)(=O)C>[CH3:11][S:10][C:2]1[S:3][C:4]2[C:9]([N:1]=1)=[CH:8][CH:7]=[CH:6][N:5]=2

Participants

6

Reactant 3

HCID 6328Methyl iodide2×HCID 11430Potassium CarbonateHCID 178527801HCID 178527801, compound

Product 1

HCID 6998402-(Methylthio)thiazolo[5,4-b]pyridineYield 100%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

To the suspension of thiazolo[5,4-b]pyridine-2-thiol (168 mg, 1.0 mmol) in THF (3.3 ml) was added potassium carbonate (193 mg, 1.4 mmol), followed by iodomethane (68.2 μl, 1.1 mmol) dropwise. The reaction mixture was stirred at room temperature for 16 h. Additional iodomethane were mixed in (40 uL) and stirred at room temperature for another 3 h. LCMS showed reaction was complete. The crude reaction mixture was suspended in ethyl acetate and washed with water, then brine, dried over sodium sulfate, filtered, and concentrated to give 2-(methylthio)thiazolo[5,4-b]pyridine (182 mg, 1.0 mmol, 100% yield) as a tan solid.

Workup

  1. stirringstirred at room temperature for another 3 h
  2. customreaction
  3. customThe crude reaction mixture
  4. washwashed with water
  5. dry with materialbrine, dried over sodium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-687eaacea0954c2181fa4689a4f58028
Source dataset
uspto-grants-2015_11
Patent number
US09174992B2

Linked notes

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