P-Anisidine → HCID 66592614, compound

HRID 1093531Notes

Reaction equation

HRID 1093531 reaction equation
Cl[C:2]1[CH:3]=[C:4]([C:8]2[N:12]3[CH:13]=[CH:14][CH:15]=[CH:16][C:11]3=[N:10][CH:9]=2)[CH:5]=[CH:6][CH:7]=1.[CH3:17][O:18][C:19]1[CH:24]=[CH:23][C:22]([NH2:25])=[CH:21][CH:20]=1.CC(C)([O-])C.[Na+]>C1(C)C=CC=CC=1>[N:10]1[CH:9]=[C:8]([C:4]2[CH:3]=[C:2]([C:23]3[CH:24]=[C:19]([O:18][CH3:17])[CH:20]=[CH:21][C:22]=3[NH2:25])[CH:7]=[CH:6][CH:5]=2)[N:12]2[CH:13]=[CH:14][CH:15]=[CH:16][C:11]=12

Participants

5

Reactant 3

HCID 7732P-AnisidineHCID 23676156Sodium t-butoxideHCID 57058598HCID 57058598, compound

Product 1

HCID 66592614HCID 66592614, compoundYield 9.9%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
110 °C

Procedure

A mixture of 3-(3-Chloro-phenyl)-imidazo[1,2-a]pyridine (183 mg, 0.8 mmol), 4-Methoxy-phenylamine (200 mg, 1.6 mmol) and sodium tertbutoxide (195 mg, 2 mmol) in dry toluene (3 ml) was deoxygenated. 2′-(Dimethylamino)-2-biphenylyl-palladium(II) chloride dinorbornylphosphine complex (45 mg, 0.08 mmol) was added and the reaction mixture deoxygenated again, then heated at 110° C. for 2 h. The mixture was allowed to cool, then partitioned between CH2Cl2 and H2O and separated using a phase separating cartridge. The organic solvent was removed in vacuo and the residue purified by column chromatography, then preparative HPLC to give the desired compound (25 mg).

Workup

  1. customwas deoxygenated
  2. addition2′-(Dimethylamino)-2-biphenylyl-palladium(II) chloride dinorbornylphosphine complex (45 mg, 0.08 mmol) was added
  3. customthe reaction mixture deoxygenated again
  4. temperatureto cool
  5. custompartitioned between CH2Cl2 and H2O
  6. customseparated
  7. customseparating cartridge
  8. customThe organic solvent was removed in vacuo
  9. customthe residue purified by column chromatography

Sources & evidence

ORD record
ord-f886d900a9904e3db1a0d7a2c61453af
Source dataset
uspto-grants-2012_03
Patent number
US08131527B1

Reaction notes

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