Methyl iodide → 5-Chloro-2-(methylsulfanyl)[1,3]thiazolo[5,4-b]pyridine

HRID 1845899Notes

Reaction equation

HRID 1845899 reaction equation
[Cl:1][C:2]1[N:7]=[C:6]2[S:8][C:9]([SH:11])=[N:10][C:5]2=[CH:4][CH:3]=1.[CH2:12]1COCC1.C(=O)([O-])[O-].[K+].[K+].CI>C(OCC)(=O)C>[Cl:1][C:2]1[N:7]=[C:6]2[S:8][C:9]([S:11][CH3:12])=[N:10][C:5]2=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 6328Methyl iodideHCID 8028TetrahydrofuranHCID 11430Potassium CarbonateHCID 178527792HCID 178527792, compound

Product 1

HCID 137996675-Chloro-2-(methylsulfanyl)[1,3]thiazolo[5,4-b]pyridine

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

To a round bottom flask was added 5-chloro[1,3]thiazolo[5,4-b]pyridine-2-thiol (1-1) (21.4 g, 106 mmol), anhydrous THF (400 mL), potassium carbonate (20.5 g, 148 mmol), followed by methyl iodide (16.9 g, 119 mmol). The reaction vessel was sealed and stirred at room temperature for 5 minutes. The crude reaction mixture was then suspended in ethyl acetate and washed with a saturated solution of sodium bicarbonate, followed by water, then brine, dried over sodium sulfate, filtered, and concentrated to give 5-chloro-2-(methylthio)[1,3]thiazolo[5,4-b]pyridine (1-2) as a pink solid. HRMS (M+H)+: observed=216.9658, calculated=216.9655.

Workup

  1. customThe reaction vessel was sealed
  2. customThe crude reaction mixture
  3. washwashed with a saturated solution of sodium bicarbonate
  4. dry with materialbrine, dried over sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-da225902e2d14846b3152c2f19e0424e
Source dataset
uspto-grants-2015_02
Patent number
US08952005B2

Reaction notes

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