1,4-Dioxane → HCID 58394290, compound

HRID 2047602Notes

Reaction equation

HRID 2047602 reaction equation
O1CCOCC1.Br[C:8]1[C:13]([C:14]([O:16][CH3:17])=[O:15])=[CH:12][C:11]([Cl:18])=[N:10][CH:9]=1.C([Sn](CCCC)(CCCC)[C:24]1[S:25][CH:26]=[CH:27][N:28]=1)CCC>CCOC(C)=O>[Cl:18][C:11]1[CH:12]=[C:13]([C:8]([C:24]2[S:25][CH:26]=[CH:27][N:28]=2)=[CH:9][N:10]=1)[C:14]([O:16][CH3:17])=[O:15]

Participants

5

Reactant 3

HCID 312751,4-DioxaneHCID 27632592-(Tributylstannyl)-1,3-thiazoleHCID 26966728Methyl 5-bromo-2-chloropyridine-4-carboxylate

Product 1

HCID 58394290HCID 58394290, compound

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Conditions

Temperature
65 °C

Procedure

To a 100 mL round bottom flask was added bis(tri-tertbutylphosphine)palladium(0) (204 mg, 0.40 mmol, 0.1 equiv). The flask was then flushed with nitrogen and charged with 1,4-dioxane (20 mL), methyl 5-bromo-2-chloroisonicotinate (7-1, 1000 mg, 4.0 mmol, 1 equiv) and 2-(tributylstannyl)-1,3-thiazole (1.5 mL, 4.8 mmol, 1.2 equiv). The reaction mixture was heated for 3 hours at 65° C., diluted with EtOAc (20 mL) and filtered through celite. The filtrate was concentrated and the residue purified by normal phase column chromatography (0-40% EtOAc in hexanes) to afford the title compound (7-2) as a yellow solid. ESI+MS[M+H]+C10H8ClN2O2S=255.0

Workup

  1. customThe flask was then flushed with nitrogen
  2. filtrationfiltered through celite
  3. concentrationThe filtrate was concentrated
  4. customthe residue purified by normal phase column chromatography (0-40% EtOAc in hexanes)

Sources & evidence

ORD record
ord-c348678643d74df89cabce2030742762
Source dataset
uspto-grants-2013_11
Patent number
US08592457B2

Reaction notes

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