Triphenylphosphine → HCID 58951434, compound

HRID 1445786Notes

Reaction equation

HRID 1445786 reaction equation
[CH2:1]([O:3][C:4](=[O:25])[CH2:5][C:6]1[N:7]=[C:8]([C:11]2[CH:16]=[CH:15][C:14](OS(C(F)(F)F)(=O)=O)=[CH:13][CH:12]=2)[O:9][CH:10]=1)[CH3:2].[CH3:26][S:27]([C:30]1[CH:35]=[CH:34][C:33](B(O)O)=[CH:32][CH:31]=1)(=[O:29])=[O:28].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[F-].[Cs+]>CN(C=O)C.C([O-])(=O)C.[Pd+2].C([O-])(=O)C>[CH2:1]([O:3][C:4](=[O:25])[CH2:5][C:6]1[N:7]=[C:8]([C:11]2[CH:12]=[CH:13][C:14]([C:33]3[CH:34]=[CH:35][C:30]([S:27]([CH3:26])(=[O:29])=[O:28])=[CH:31][CH:32]=3)=[CH:15][CH:16]=2)[O:9][CH:10]=1)[CH3:2]

Participants

7

Reactant 4

HCID 11776TriphenylphosphineHCID 25953Cesium fluorideHCID 27343644-(Methanesulfonyl)phenylboronic acidHCID 58951469HCID 58951469, compound2×

Product 1

HCID 58951434HCID 58951434, compoundYield 12%

Reagents, catalysts & solvents 2

HCID 167845palladium(II) acetateCatalystHCID 6228DimethylformamideSolvent

Conditions

Temperature
110 °C

Procedure

A suspension of [2-(4-Trifluoromethanesulfonyloxy-phenyl)-oxazol-4-yl]-acetic acid ethyl ester (See Intermediate 69) (0.83 g, 2.2 mmol), 4-(methanesulfonyl)phenyl boronic acid (0.48 g, 2.4 mmol), triphenylphosphine (69 mg, 0.26 mmol), cesium fluoride (0.67 g, 4.4 mmol) and palladium acetate (15 mg, 0.066 mmol) in DMF (10 mL) is heated at 110° C. for 24 h. The suspension is cooled to room temperature and filtered. The filtrate is partitioned between EtOAc and water. The aqueous phase is extracted with EtOAc. The combined organic phase is washed with brine, dried (Na2SO4), and concentrated. The residue is purified by flash chromatography (40 g SiO2, elute 20% to 80% EtOAC/hexane) to yield the title compound (0.10 g, 12%). MS (m/e): 386.2 (M+1)

Workup

  1. temperatureThe suspension is cooled to room temperature
  2. filtrationfiltered
  3. customThe filtrate is partitioned between EtOAc and water
  4. extractionThe aqueous phase is extracted with EtOAc
  5. washThe combined organic phase is washed with brine
  6. dry with materialdried (Na2SO4)
  7. concentrationconcentrated
  8. customThe residue is purified by flash chromatography (40 g SiO2, elute 20% to 80% EtOAC/hexane)

Sources & evidence

ORD record
ord-d00e7df4ee414e7a90c9f43ea95f3ae5
Source dataset
uspto-grants-2010_02
Patent number
US07666871B2

Reaction notes

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