Pivalic acid → HCID 86669128, compound

HRID 2400352Notes

Reaction equation

HRID 2400352 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][N:5]2[C:8](I)=[CH:9][N:10]=[C:4]2[CH:3]=1.C[N:13]([C:15]1C(C2C(P(C3CCCCC3)C3CCCCC3)=CC=CC=2)=CC=C[CH:16]=1)C.C(=O)([O-])[O-].[Cs+].[Cs+].C(O)(=O)C(C)(C)C.[C:53]([NH:56][C:57]1[S:58][CH:59]=[CH:60][N:61]=1)(=[O:55])C>C([O-])(=O)C.[Pd+2].C([O-])(=O)C.CC(N(C)C)=O>[ClH:1].[Cl:1][C:2]1[CH:7]=[CH:6][N:5]2[C:8]([C:59]3[S:58][C:57]([NH:56][C:53]([NH:13][CH2:15][CH3:16])=[O:55])=[N:61][CH:60]=3)=[CH:9][N:10]=[C:4]2[CH:3]=1

Participants

8

Reactant 5

HCID 6417Pivalic acidHCID 10796Cesium carbonateHCID 176252-AcetamidothiazoleHCID 27342172-(Dicyclohexylphosphino)-2'-(dimethylamino)biphenylHCID 574976977-Chloro-3-iodoimidazo[1,2-a]pyridine

Product 1

HCID 86669128HCID 86669128, compound

Reagents, catalysts & solvents 2

HCID 167845palladium(II) acetateCatalystHCID 31374DimethylacetamideSolvent

Conditions

Temperature
110 °C

Procedure

A mixture of the iodide (From Procedure A2, 1.06 g, 3.81 mmol), palladium acetate (catalytic amount), DavePhos (catalytic amount), cesium carbonate (1.86 g, 5.71 mmol), pivalic acid (583 mg, 5.71 mmol), dimethylacetamide (20 ml) and 2-acetamidothiazole (1.56 g, 9.52 mmol) was heated to 110° C. under nitrogen overnight. The reaction was then allowed to cool. The reaction was filtered under suction washing with ethyl acetate and water. These solids were discarded and the liquors were re-filtered to furnish some crude product. The liquors were taken; the ethyl acetate layer separated and was washed with 10% aqueous lithium chloride and brine. This solution was dried (MgSO4) and concentrated in vacuo. The residue was triturated with dichloromethane to furnish the desired product (500 mg). MS: [M+H]+=293.

Workup

  1. temperatureto cool
  2. filtrationThe reaction was filtered under suction
  3. washwashing with ethyl acetate and water
  4. filtrationthe liquors were re-filtered
  5. customto furnish some crude product
  6. customthe ethyl acetate layer separated
  7. washwas washed with 10% aqueous lithium chloride and brine
  8. dry with materialThis solution was dried (MgSO4)
  9. concentrationconcentrated in vacuo
  10. customThe residue was triturated with dichloromethane

Sources & evidence

ORD record
ord-7213c99bbf894b009fef26466f4257ee
Source dataset
uspto-grants-2014_08
Patent number
US08796244B2

Reaction notes

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