Cesium carbonate → HCID 66748949, compound

HRID 537076Notes

Reaction equation

HRID 537076 reaction equation
I[C:2]1[N:3]=[C:4]([C:20]2[C:25]([CH3:26])=[CH:24][N:23]=[C:22]([NH:27][C:28](=[O:30])[CH3:29])[CH:21]=2)[O:5][C:6]=1[C:7]1[N:11]=[CH:10][N:9]([CH2:12][O:13][CH2:14][CH2:15][Si:16]([CH3:19])([CH3:18])[CH3:17])[N:8]=1.CC1(C)C2C(=C(P(C3C=CC=CC=3)C3C=CC=CC=3)C=CC=2)OC2C(P(C3C=CC=CC=3)C3C=CC=CC=3)=CC=CC1=2.[S:73]1(=[O:79])(=[O:78])[CH2:77][CH2:76][CH2:75][NH:74]1.C(=O)([O-])[O-].[Cs+].[Cs+]>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]>[O:78]=[S:73]1(=[O:79])[CH2:77][CH2:76][CH2:75][N:74]1[C:2]1[N:3]=[C:4]([C:20]2[C:25]([CH3:26])=[CH:24][N:23]=[C:22]([NH:27][C:28](=[O:30])[CH3:29])[CH:21]=2)[O:5][C:6]=1[C:7]1[N:11]=[CH:10][N:9]([CH2:12][O:13][CH2:14][CH2:15][Si:16]([CH3:17])([CH3:19])[CH3:18])[N:8]=1

Participants

7

Reactant 4

HCID 10796Cesium carbonateHCID 6360441,1'-(9,9-Dimethyl-9H-xanthene-4,5-diyl)bis(1,1-diphenylphosphine)HCID 6421571,3-PropanesultamHCID 66749237HCID 66749237, compound

Product 1

HCID 66748949HCID 66748949, compound

Reagents, catalysts & solvents 2

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

Procedure

To a solution of N-{4-[4-iodo-5-(1-{[2-(trimethylsilyl)ethoxy]methyl}-1H-1,2,4-triazol-3-yl)-1,3-oxazol-2-yl]-5-methylpyridin-2-yl}acetamide (0.33 g, 0.601 mmol) in 1,4-dioxane (4 mL) was added tris(dibenzylideneacetone)dipalladium(0) (0.055 g, 0.060 mmol), Xantphos (0.10 g, 0.18 mmol), isothiazolidine 1,1-dioxide (0.36 g, 3.01 mmol) and cesium carbonate (0.98 g, 3.00 mmol). The mixture was degassed with nitrogen and then subjected to microwave irradiation at 140° C. for 2.5 h. The mixture was diluted with water and extracted with EtOAc. The organic solutions were combined, dried over MgSO4, filtered and concentrated. The residue was purified by column chromatography to give N-{4-[4-(1,1-dioxidoisothiazolidin-2-yl)-5-(1-{[2-(trimethylsilyl)ethoxy]methyl}-1H-1,2,4-triazol-3-yl)-1,3-oxazol-2-yl]-5-methylpyridin-2-yl}acetamide which was used directly in the next step. LCMS (FA): m/z=534.6 (M+H).

Workup

  1. customThe mixture was degassed with nitrogen
  2. customirradiation at 140° C. for 2.5 h
  3. additionThe mixture was diluted with water
  4. extractionextracted with EtOAc
  5. dry with materialdried over MgSO4
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customThe residue was purified by column chromatography

Sources & evidence

ORD record
ord-4dffa67bb41646a69903286ef42f3ac4
Source dataset
uspto-grants-2014_10
Patent number
US08859768B2

Reaction notes

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