Cesium carbonate → HCID 67106507, compound

HRID 2388899Notes

Reaction equation

HRID 2388899 reaction equation
[O:1]1[C:5]2([CH2:10][CH2:9][N:8]([S:11]([NH2:14])(=[O:13])=[O:12])[CH2:7][CH2:6]2)[O:4][CH2:3][CH2:2]1.C1(P(C2CCCCC2)C2C=CC=CC=2C2C(C(C)C)=CC(C(C)C)=CC=2C(C)C)CCCCC1.C(=O)([O-])[O-].[Cs+].[Cs+].Cl[C:56]1[CH:61]=[C:60]([O:62][CH3:63])[N:59]=[C:58]([S:64][CH2:65][C:66]2[CH:71]=[CH:70][CH:69]=[C:68]([F:72])[C:67]=2[F:73])[N:57]=1.[Cl-].[NH4+]>O1CCOCC1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd]>[F:73][C:67]1[C:68]([F:72])=[CH:69][CH:70]=[CH:71][C:66]=1[CH2:65][S:64][C:58]1[N:57]=[C:56]([NH:14][S:11]([N:8]2[CH2:7][CH2:6][C:5]3([O:4][CH2:3][CH2:2][O:1]3)[CH2:10][CH2:9]2)(=[O:12])=[O:13])[CH:61]=[C:60]([O:62][CH3:63])[N:59]=1

Participants

8

Reactant 5

HCID 10796Cesium carbonateHCID 25517Ammonium ChlorideHCID 111557942-Dicyclohexylphosphino-2',4',6'-triisoprophylbiphenylHCID 20782267HCID 20782267, compound2×HCID 866198774-Chloro-2-([(2,3-difluorophenyl)methyl]thio]-6-methoxypyrimidine2×

Product 1

HCID 67106507HCID 67106507, compound

Reagents, catalysts & solvents 2

HCID 9811564Bis(dibenzylideneacetone)palladiumCatalystHCID 312751,4-DioxaneSolvent

Conditions

Temperature
100 °C

Procedure

A mixture of 1,4-dioxa-8-azaspiro[4.5]decane-8-sulfonamide (the product of step i), (0.29 g), tris(dibenzylideneacetone)-dipalladium (0) (61 mg), 2-dicyclohexylphosphino-2′,4′,6′-tri-isopropyl-1,1′-biphenyl (XPHOS) (32 mg), cesium carbonate (0.32 g) and 4-chloro-2-[[(2,3-difluorophenyl)methyl]thio]-6-methoxypyrimidine (the product of example 35 step i, 0.20 g) in anhydrous dioxane (8 mL) was heated at reflux in a microwave at 100° C., 300 W, open vessel with cooling for 15 min. Saturated aqueous ammonium chloride was added and the resulting mixture extracted with ethyl acetate. The combined organic extracts were washed with saturated aqueous sodium chloride, dried with sodium sulfate, filtered and evaporated.

Workup

  1. temperaturewas heated
  2. temperature300 W, open vessel with cooling for 15 min
  3. extractionthe resulting mixture extracted with ethyl acetate
  4. washThe combined organic extracts were washed with saturated aqueous sodium chloride
  5. dry with materialdried with sodium sulfate
  6. filtrationfiltered
  7. customevaporated

Sources & evidence

ORD record
ord-8e935813d15f419e92df03a8fd9c232f
Source dataset
uspto-grants-2012_09
Patent number
US08269002B2

Reaction notes

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