Cesium carbonate → HCID 68448655, compound

HRID 2233185Notes

Reaction equation

HRID 2233185 reaction equation
[C:1]([O:4][CH2:5][C:6]1[CH:11]=[C:10](OS(C(F)(F)F)(=O)=O)[C:9]([O:20][CH2:21][CH2:22][NH:23][C:24]([O:26][C:27]([CH3:30])([CH3:29])[CH3:28])=[O:25])=[CH:8][N:7]=1)(=[O:3])[CH3:2].C(=O)([O-])[O-].[Cs+].[Cs+]>C1(C)C=CC=CC=1.C([O-])(=O)C.[Pd+2].C([O-])(=O)C.C1(P(C2C=CC=CC=2)C2C=CC3C(=CC=CC=3)C=2C2C3C(=CC=CC=3)C=CC=2P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>[C:1]([O:4][CH2:5][C:6]1[N:7]=[CH:8][C:9]2[O:20][CH2:21][CH2:22][N:23]([C:24]([O:26][C:27]([CH3:30])([CH3:29])[CH3:28])=[O:25])[C:10]=2[CH:11]=1)(=[O:3])[CH3:2]

Participants

6

Reactant 2

HCID 10796Cesium carbonateHCID 86623072HCID 86623072, compound

Product 1

HCID 68448655HCID 68448655, compoundYield 80.1%

Reagents, catalysts & solvents 3

HCID 167845palladium(II) acetateCatalystHCID 634876Binap, (A+-)-CatalystHCID 1140TolueneSolvent

Conditions

Temperature
100 °C

Procedure

A mixture of (5-{[2-({[(1,1-dimethylethyl)oxy]carbonyl}amino)ethyl]oxy}-4-{[(trifluoromethyl)sulfonyl]oxy}-2-pyridinyl)methyl acetate (1.58 g, 3.4 mmol), (±)-2,2′-bis(diphenylphosphino)-1,1′-binaphthalene (BI NAP) (110 mg, 0.2 mmol), palladium(II) acetate (25 mg, 0.1 mmol) and cesium carbonate (1.57 g, 4.8 mmol) in toluene (20 ml) was heated to 100° C. under argon for 16 hours then filtered and evaporated. (See S. L. Buchwald, Org Letts, 1999, 1, 35-37; for the procedure). The residue was chromatographed on silica gel, eluting with 0-100% ethyl acetate in petrol, to afford a white solid (0.84 g, 79%)

Workup

  1. filtrationthen filtered
  2. customevaporated
  3. customThe residue was chromatographed on silica gel
  4. washeluting with 0-100% ethyl acetate in petrol

Sources & evidence

ORD record
ord-1061193a22c24f2a8df0600b7d831cd3
Source dataset
uspto-grants-2010_05
Patent number
US07709483B2

Reaction notes

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