Cesium carbonate → Ethyl 5-chlorothiazolo[5,4-b]pyridine-2-carboxylate

HRID 1177399Notes

Reaction equation

HRID 1177399 reaction equation
Cl[C:2]1[C:7]([NH:8][C:9](=[S:15])[C:10]([O:12][CH2:13][CH3:14])=[O:11])=[CH:6][CH:5]=[C:4]([Cl:16])[N:3]=1.C(=O)([O-])[O-].[Cs+].[Cs+]>C1COCC1.O>[Cl:16][C:4]1[N:3]=[C:2]2[S:15][C:9]([C:10]([O:12][CH2:13][CH3:14])=[O:11])=[N:8][C:7]2=[CH:6][CH:5]=1

Participants

5

Reactant 2

HCID 10796Cesium carbonateHCID 86638703Ethyl 2-(2,6-dichloropyridin-3-ylamino)-2-thioxoacetate

Product 1

HCID 86638705Ethyl 5-chlorothiazolo[5,4-b]pyridine-2-carboxylate

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
50 °C

Procedure

A mixture of ethyl 2-(2,6-dichloropyridin-3-ylamino)-2-thioxoacetate (49.11 g, 175.9 mmol) and cesium carbonate (57.32 g, 175.9 mmol) in THF (350 mL) was heated at 50° C. for 6 h. The reaction suspension was then diluted with water (700 mL) and THF was removed in vacuo at 23° C. The resulting suspension was cooled to 0° C., and the precipitated solid was collected via vacuum filtration, washed with water, and dried in vacuo to provide ethyl 5-chlorothiazolo[5,4-b]pyridine-2-carboxylate as a yellow-orange solid. MS (ESI) m/z: Calculated: 242.0; Observed: 243.0 (M++1).

Workup

  1. customwas removed in vacuo at 23° C
  2. temperatureThe resulting suspension was cooled to 0° C.
  3. filtrationthe precipitated solid was collected via vacuum filtration
  4. washwashed with water
  5. customdried in vacuo

Sources & evidence

ORD record
ord-06a24c6ee96841288b3bed411e27d24d
Source dataset
uspto-grants-2010_11
Patent number
US07842685B2

Reaction notes

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