Methyl iodide → Ethyl 2-(methylthio)thiazolo[4,5-b]pyridine-6-carboxylate

HRID 1848103Notes

Reaction equation

HRID 1848103 reaction equation
[K].[SH:2][C:3]1[S:4][C:5]2[C:6]([N:16]=1)=[N:7][CH:8]=[C:9]([C:11]([O:13][CH2:14][CH3:15])=[O:12])[CH:10]=2.I[CH3:18]>CN(C=O)C>[CH3:18][S:2][C:3]1[S:4][C:5]2[C:6]([N:16]=1)=[N:7][CH:8]=[C:9]([C:11]([O:13][CH2:14][CH3:15])=[O:12])[CH:10]=2

Participants

4

Reactant 2

HCID 6328Methyl iodideHCID 178469699HCID 178469699, compound

Product 1

HCID 86681077Ethyl 2-(methylthio)thiazolo[4,5-b]pyridine-6-carboxylateYield 82%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
0 °C

Procedure

To a stirred mixture of ethyl 2-mercaptothiazolo[4,5-b]pyridine-6-carboxylate potassium salt (1.7 g, 6.6 mmol) from the previous step in DMF (10 mL) at 0° C. was added iodomethane (226 μL, 3.6 mmol). After the mixture was stirred at 0° C. for 2 h, it was allowed to warm slowly to rt. The mixture was partitioned between EtOAc (100 mL) and 0.5 M aq Na2CO3 (50 mL). The organic layer was separated and washed with brine (50 mL), dried over Mg2SO4, filtered, and concentrated under reduced pressure to afford ethyl 2-(methylthio)thiazolo[4,5-b]pyridine-6-carboxylate (724 mg, 82%) as a yellow solid. The material was used in the next step without further purification. 1H NMR (300 MHz, DMSO-d6) δ 9.07 (s, 2H), 4.38 (q, J=7.0 Hz, 2H), 2.86 (s, 3H), 1.36 (t, J=7.1 Hz, 3H); LCMS (ESI) m/z 255 (M+H)+.

Workup

  1. temperatureto warm slowly to rt
  2. customThe mixture was partitioned between EtOAc (100 mL) and 0.5 M aq Na2CO3 (50 mL)
  3. customThe organic layer was separated
  4. washwashed with brine (50 mL)
  5. dry with materialdried over Mg2SO4
  6. filtrationfiltered
  7. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-5794925101be4877a64e786ce04ea489
Source dataset
uspto-grants-2015_02
Patent number
US08952058B2

Reaction notes

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