Cesium carbonate → HCID 68870828, compound

HRID 730003

Reaction equation

HRID 730003 reaction equation
[C:1]([C:5]1[O:6][CH:7]=[C:8]([C:10]2[CH:15]=[CH:14][C:13]([F:16])=[CH:12][CH:11]=2)[N:9]=1)([CH3:4])([CH3:3])[CH3:2].Br[C:18]1[N:23]=[C:22]2[N:24]([CH2:28][CH:29]([CH3:31])[CH3:30])[C:25]([NH2:27])=[N:26][C:21]2=[CH:20][CH:19]=1.C(=O)([O-])[O-].[Cs+].[Cs+].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>CN(C=O)C.C([O-])(=O)C.[Pd+2].C([O-])(=O)C>[C:1]([C:5]1[O:6][C:7]([C:18]2[N:23]=[C:22]3[N:24]([CH2:28][CH:29]([CH3:31])[CH3:30])[C:25]([NH2:27])=[N:26][C:21]3=[CH:20][CH:19]=2)=[C:8]([C:10]2[CH:11]=[CH:12][C:13]([F:16])=[CH:14][CH:15]=2)[N:9]=1)([CH3:4])([CH3:2])[CH3:3]

Participants

7

Reactant 4

HCID 10796Cesium carbonateHCID 11776TriphenylphosphineHCID 668690432-tert-Butyl-4-(4-fluorophenyl)oxazoleHCID 86063644HCID 86063644, compound

Product 1

HCID 68870828HCID 68870828, compoundYield 34%

Reagents, catalysts & solvents 2

HCID 167845palladium(II) acetateCatalystHCID 6228DimethylformamideSolvent

Procedure

Bubble with nitrogen a suspension of 2-tert-butyl-4-(4-fluorophenyl)oxazole (0.145 g, 0.66 mmol), 5-bromo-3-isobutyl-3H-imidazo[4,5-b]pyridin-2-ylamine (0.355 g, 1.32 mmol), cesium carbonate (6.06 g, 18.6 mmol), palladium (II) acetate (0.201 g, 10%) and triphenylphosphine (0.14 g, 0.07 mmol) in DMF (1.5 mL). Heat the reaction at 100° C. overnight, cool to RT and partition between EtOAc and saturated aqueous NaCl. Wash the organic layer with saturated aqueous NaCl. Dry with Na2SO4, filter, concentrate, and purify (silica gel chromatography, eluting with 2% of 2M ammonia/MeOH in CH2Cl2 to give the title compound (0.07 g, 34%).

Workup

  1. customBubble with nitrogen
  2. temperatureHeat
  3. customthe reaction at 100° C. overnight
  4. custompartition between EtOAc and saturated aqueous NaCl
  5. washWash the organic layer with saturated aqueous NaCl
  6. dry with materialDry with Na2SO4
  7. filtrationfilter
  8. concentrationconcentrate
  9. custompurify (silica gel chromatography
  10. washeluting with 2% of 2M ammonia/MeOH in CH2Cl2

Sources & evidence

ORD record
ord-ebea77b7d7c54cd391eaca0d172e8e47
Source dataset
uspto-grants-2009_09
Patent number
US07582652B2

Linked notes

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