Potassium Carbonate → HCID 10022197, compound

HRID 915263Notes

Reaction equation

HRID 915263 reaction equation
[Cl:1][C:2]1[C:3]([NH:8][C:9]2[S:10][CH:11]=[C:12]([C:14]([O:16]CC)=O)[N:13]=2)=[N:4][CH:5]=[CH:6][CH:7]=1.NC1S[CH:22]=[C:23]([C:25](OCC)=O)[N:24]=1.ClC1C(Cl)=CC=CN=1.C1(P(C2C=CC=CC=2)[C:45]2C=C[C:52]3[C:47](=[CH:48]C=CC=3)[C:46]=2[C:55]2C3C(=CC=CC=3)C=CC=2P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C(=O)([O-])[O-].[K+].[K+]>C([O-])(=O)C.[Pd+2].C([O-])(=O)C.C1(C)C=CC=CC=1>[Cl:1][C:2]1[C:3]([NH:8][C:9]2[S:10][CH:11]=[C:12]([C:14]([NH:25][C:23]3[CH:22]=[CH:55][C:46]([CH:47]([CH3:52])[CH3:48])=[CH:45][CH:24]=3)=[O:16])[N:13]=2)=[N:4][CH:5]=[CH:6][CH:7]=1

Participants

8

Reactant 5

HCID 11430Potassium CarbonateHCID 169882,3-DichloropyridineHCID 73216Ethyl 2-aminothiazole-4-carboxylateHCID 634876Binap, (A+-)-HCID 58958520HCID 58958520, compound

Product 1

HCID 10022197HCID 10022197, compound

Reagents, catalysts & solvents 2

HCID 167845palladium(II) acetateCatalystHCID 1140TolueneSolvent

Conditions

Temperature
112 °C

Procedure

Ethyl 2-[(3-chloro-2-pyridyl)amino]-1,3-thiazole-4-carboxylate. A mixture of ethyl 2-amino-1,3-thiazole-4-carboxylate (2.33 g, 13.5 mmol), 2,3-dichloro-pyridine (2.0 g, 13.5 mmol, Lancaster), palladium (II) acetate (152 mg, 0.68 mmol, Strem Chemicals), rac-2,2′-bis(diphenylphosphino)-1,1′-binaphthyl (420 mg, 0.68 mmol, Aldrich), potassium carbonate (37.3 g, Mallinckrodt) and toluene (55 mL) in a sealed flask was stirred at 112° C. under N2 for 2 d. The reaction mixture was passed through a pad of Celite and the Celite pad was washed with EtOAc (5×100 mL). The organic layer was diluted with H2O (200 mL), and separated from the aqueous phase. The aqueous phase was extracted with EtOAc (150 mL). The combined organic phase was washed with satd NaCl (200 mL), dried over Na2SO4, filtered and concentrated in vacuo. Purification by silica gel chromatography (0-15% EtOAc in hexane) provided the title compound as a white solid. MS (ESI, pos. ion) m/z: 284 (M+1).

Workup

  1. washthe Celite pad was washed with EtOAc (5×100 mL)
  2. additionThe organic layer was diluted with H2O (200 mL)
  3. customseparated from the aqueous phase
  4. extractionThe aqueous phase was extracted with EtOAc (150 mL)
  5. washThe combined organic phase was washed with satd NaCl (200 mL)
  6. dry with materialdried over Na2SO4
  7. filtrationfiltered
  8. concentrationconcentrated in vacuo
  9. customPurification by silica gel chromatography (0-15% EtOAc in hexane)

Sources & evidence

ORD record
ord-69b674907d84419b894c2c4615656938
Source dataset
uspto-grants-2007_09
Patent number
US07265138B2

Reaction notes

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