Cesium carbonate → HCID 117824027, compound

HRID 59128Notes

Reaction equation

HRID 59128 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:7]=[CH:8][C:9]=1[N:10]1[CH:14]=[C:13]([CH3:15])[N:12]=[CH:11]1)[NH2:6].Cl[C:17]1[N:22]=[C:21]([CH2:23][C:24]([O:26][CH2:27][CH3:28])=[O:25])[CH:20]=[C:19]([CH2:29][O:30][CH2:31][C:32]([F:35])([F:34])[F:33])[N:18]=1.C([O-])([O-])=O.[Cs+].[Cs+].C1CCC(P(C2C(C3C=CC=CC=3)=CC=CC=2)C2CCCCC2)CC1>O1CCOCC1.C([O-])(=O)C.[Pd+2].C([O-])(=O)C>[CH3:1][O:2][C:3]1[CH:4]=[C:5]([NH:6][C:17]2[N:22]=[C:21]([CH2:23][C:24]([O:26][CH2:27][CH3:28])=[O:25])[CH:20]=[C:19]([CH2:29][O:30][CH2:31][C:32]([F:35])([F:33])[F:34])[N:18]=2)[CH:7]=[CH:8][C:9]=1[N:10]1[CH:14]=[C:13]([CH3:15])[N:12]=[CH:11]1

Participants

7

Reactant 4

HCID 10796Cesium carbonateHCID 27342162-(Dicyclohexylphosphino)biphenylHCID 454801813-methoxy-4-(4-methyl-1H-imidazol-1-yl)anilineHCID 117821132HCID 117821132, compound

Product 1

HCID 117824027HCID 117824027, compound

Reagents, catalysts & solvents 2

HCID 167845palladium(II) acetateCatalystHCID 312751,4-DioxaneSolvent

Conditions

Temperature
120 °C

Procedure

Palladium acetate (21 mg, 0.095 mmol) was added to a degassed solution of 3-methoxy-4-(4-methyl-1H-imidazol-1-yl)aniline (155 mg, 0.76 mmol), ethyl 2-{2-chloro-6-[(2,2,2-trifluoro-ethoxy)methyl]pyrimidin-4-yl}acetate (180 mg, 0.63 mmol), Cs2CO3 (411 mg, 1.26 mmol), (2-biphenyl)dicyclohexylphosphine (33 mg, 0.95 mmol) in 1,4-dioxane (4 mL). The microwave tube was capped and the heterogeneous solution was immersed in a sonic bath for 2 min prior to heating it in a microwave reactor at 120° C. for 1.5 h. The reaction was cooled down to rt and concentrated in vacuo with diatomaceous earth. The resulting mixture was purified on silica gel eluting with 0% to 5% MeOH/DCM (1% ammonium hydroxide). The residue obtained was purified on a C18 reverse phase cartridge eluting with 0% to 40% MeOH/H2O (containing 0.05% TFA) to give the title compound as a gum, 110 mg (38%).

Workup

  1. customThe microwave tube was capped
  2. temperatureThe reaction was cooled down to rt
  3. concentrationconcentrated in vacuo with diatomaceous earth
  4. customThe resulting mixture was purified on silica gel eluting with 0% to 5% MeOH/DCM (1% ammonium hydroxide)
  5. customThe residue obtained
  6. customwas purified on a C18 reverse phase cartridge
  7. washeluting with 0% to 40% MeOH/H2O (containing 0.05% TFA)

Sources & evidence

ORD record
ord-31756b2590ad4c049a9ef7448b7baec4
Source dataset
uspto-grants-2016_09
Patent number
US09439904B2

Reaction notes

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