Hydroquinone → HCID 68839539, compound

HRID 660578Notes

Reaction equation

HRID 660578 reaction equation
[Si:1]([O:8][CH2:9][C@H:10]([NH:18][C:19](=[O:27])[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][C:21]=1I)[C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=1I)([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2].C1(C=CC(O)=CC=1)O.C([O-])([O-])=O.[Cs+].[Cs+].C1(C)C=CC=CC=1P(C1C=CC=CC=1C)C1C=CC=CC=1C>CN(C=O)C.CC([O-])=O.CC([O-])=O.[Pd+2]>[Si:1]([O:8][CH2:9][C@@H:10]1[NH:18][C:19](=[O:27])[C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][C:21]=2[C:12]2[CH:13]=[CH:14][CH:15]=[CH:16][C:11]1=2)([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2]

Participants

7

Reactant 4

HCID 785HydroquinoneHCID 10796Cesium carbonateHCID 80271Tri-o-tolylphosphineHCID 68838718HCID 68838718, compound

Product 1

HCID 68839539HCID 68839539, compound

Reagents, catalysts & solvents 2

HCID 167845palladium(II) acetateCatalystHCID 6228DimethylformamideSolvent

Conditions

Temperature
100 °C

Procedure

To a mixture of N—[(R)-2-(tert-butyldimethylsilanyloxy)-1-(2-iodophenyl)-ethyl]-2-iodobenzamide (60 mg, 0.159 mmol), hydroquinone (6 mg, 0.054 mmol) and Cs2CO3 (33 mg, 0.10 mmol) is added a homogenous pre-stirred solution of Pd(OAc)2 (1 mg, 0.0044 mmol) and tri-o-tolylphosphine (2 mg, 0.0065 mmol) in DMF (0.5 mL). The reaction mixture is degassed and heated under N2 at 100° C. for 5 h. The reaction mixture is cooled to RT, quenched with 2N HCl, diluted with H2O, and extracted with EtOAc. The organic phase is washed with 1N NaOH, H2O and brine, dried over MgSO4, filtered and concentrated. The crude material is purified by flash chromatography using a gradient of 0-100% . EtOAc/hexane as eluent to give the title compound as a yellow oil: (M+1)+=354.

Workup

  1. customThe reaction mixture is degassed
  2. temperatureThe reaction mixture is cooled to RT
  3. customquenched with 2N HCl
  4. additiondiluted with H2O
  5. extractionextracted with EtOAc
  6. washThe organic phase is washed with 1N NaOH, H2O and brine
  7. dry with materialdried over MgSO4
  8. filtrationfiltered
  9. concentrationconcentrated
  10. customThe crude material is purified by flash chromatography

Sources & evidence

ORD record
ord-365b0cc7722a4347b60ba5c5b78418c9
Source dataset
uspto-grants-2011_12
Patent number
US08084448B2

Reaction notes

Loading…