Toluene → Tert-butyl 4-(4-(dimethylamino)phenyl)-2-(4-fluoroanilino)benzoate

HRID 2191768Notes

Reaction equation

HRID 2191768 reaction equation
C1(C)C=CC=CC=1.Br[C:9]1[CH:21]=[CH:20][C:12]([C:13]([O:15][C:16]([CH3:19])([CH3:18])[CH3:17])=[O:14])=[C:11]([NH:22][C:23]2[CH:28]=[CH:27][C:26]([F:29])=[CH:25][CH:24]=2)[CH:10]=1.[CH3:30][N:31]([CH3:41])[C:32]1[CH:37]=[CH:36][C:35](B(O)O)=[CH:34][CH:33]=1.C(=O)([O-])O.[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.O.C(OCC)(=O)C.C(O)C>[CH3:30][N:31]([CH3:41])[C:32]1[CH:37]=[CH:36][C:35]([C:9]2[CH:21]=[CH:20][C:12]([C:13]([O:15][C:16]([CH3:19])([CH3:18])[CH3:17])=[O:14])=[C:11]([NH:22][C:23]3[CH:28]=[CH:27][C:26]([F:29])=[CH:25][CH:24]=3)[CH:10]=2)=[CH:34][CH:33]=1

Participants

9

Reactant 4

HCID 1140TolueneHCID 516892Sodium BicarbonateHCID 27343444-(Dimethylamino)phenylboronic acidHCID 68956988Tert-butyl 4-bromo-2-(4-fluoroanilino)benzoate

Product 1

HCID 68965065Tert-butyl 4-(4-(dimethylamino)phenyl)-2-(4-fluoroanilino)benzoate

Reagents, catalysts & solvents 4

HCID 178418397HCID 178418397, compoundCatalystHCID 702EthanolSolventHCID 962WaterSolvent2×HCID 8857Ethyl AcetateSolvent

Procedure

To toluene 1.6 mL solution of tert-butyl 4-bromo-2-(4-fluoroanilino)benzoate 70 mg were added ethanol 0.60 mL, water 0.30 mL, 4-(dimethylamino)phenylboronic acid 47 mg, sodium hydrogen carbonate 48 mg and tetrakis(triphenylphosphine)palladium(0) 11 mg at room temperature, and it was heated and refluxed for 6 hours. After the reaction mixture was cooled to room temperature, ethyl acetate and water were added to it. The organic layer was separated and collected,dried over anhydrous magnesium sulfate after washing with saturated sodium chloride aqueous solution, and the solvent was removed under reduced pressure. The obtained residue was refined by silica gel column chromatography [Fuji SILYSIA Chemical Ltd., PSQ100B(spherical type), eluent; hexane:ethyl acetate=10:1] to give tert-butyl 4-(4-(dimethylamino)phenyl)-2-(4-fluoroanilino)benzoate.

Workup

  1. temperatureit was heated
  2. temperaturerefluxed for 6 hours
  3. customThe organic layer was separated
  4. washafter washing with saturated sodium chloride aqueous solution
  5. customthe solvent was removed under reduced pressure

Sources & evidence

ORD record
ord-fba4b05860464168ae93855018b92540
Source dataset
uspto-grants-2012_12
Patent number
US08327467B2

Reaction notes

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