Ethanol → HCID 66592299, compound

HRID 1093526Notes

Reaction equation

HRID 1093526 reaction equation
[CH:1]1[CH:6]=[CH:5][C:4]([NH:7][C:8]2[CH:13]=[CH:12][CH:11]=[C:10](Br)[CH:9]=2)=[CH:3][CH:2]=1.[N:15]1[CH:16]=[C:17](B(O)O)[N:18]2[CH:23]=[CH:22][CH:21]=[CH:20][C:19]=12.CCO.C([O-])([O-])=O.[Na+].[Na+]>C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.C1(C)C=CC=CC=1>[N:15]1[CH:16]=[C:17]([C:10]2[CH:9]=[C:8]([NH:7][C:4]3[CH:5]=[CH:6][CH:1]=[CH:2][CH:3]=3)[CH:13]=[CH:12][CH:11]=2)[N:18]2[CH:23]=[CH:22][CH:21]=[CH:20][C:19]=12

Participants

7

Reactant 4

HCID 702EthanolHCID 10340Sodium CarbonateHCID 149586063-Bromo-N-phenylanilineHCID 55255075Imidazo[1,2-a]pyridin-3-ylboronic acid

Product 1

HCID 66592299HCID 66592299, compoundYield 2.3%

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 1140TolueneSolvent

Conditions

Temperature
80 °C

Procedure

To 3-Bromodiphenylamine (0.16 g, 0.6 mmol) was added imidazo[1,2-a]pyridine-3-ylboronic acid (0.1 g, 0.6 mmol), tetrakis(triphenylphosphine)palladium (0) (35 mg, 5 mol %), EtOH (0.5 ml), toluene (0.5 ml) and 2M Na2CO3 (0.9 ml). The reaction mixture was heated at 80° C. for 6 h, before being allowed to cool and then partitioned between EtOAc and H2O. The organic fraction was separated, washed with brine, dried (MgSO4), filtered and the solvent removed in vacuo. The residue was purified by silica column chromatography (20%-100% EtOAc/hexane) to afford the product (4 mg). MS: [M+H]+ 286.

Workup

  1. temperatureto cool
  2. custompartitioned between EtOAc and H2O
  3. customThe organic fraction was separated
  4. washwashed with brine
  5. dry with materialdried (MgSO4)
  6. filtrationfiltered
  7. customthe solvent removed in vacuo
  8. customThe residue was purified by silica column chromatography (20%-100% EtOAc/hexane)

Sources & evidence

ORD record
ord-828f594dab914ccaa3106d82b3e6b819
Source dataset
uspto-grants-2012_03
Patent number
US08131527B1

Reaction notes

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