Sodium Carbonate → 3-(3,5-Dimethyl-isoxazol-4-yl)-phenylamine

HRID 1042973Notes

Reaction equation

HRID 1042973 reaction equation
I[C:2]1[C:3]([CH3:8])=[N:4][O:5][C:6]=1[CH3:7].[NH2:9][C:10]1[CH:11]=[C:12](B(O)O)[CH:13]=[CH:14][CH:15]=1.C([O-])([O-])=O.[Na+].[Na+]>COCCOC.O.[Pd].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>[CH3:8][C:3]1[C:2]([C:14]2[CH:15]=[C:10]([CH:11]=[CH:12][CH:13]=2)[NH2:9])=[C:6]([CH3:7])[O:5][N:4]=1

Participants

7

Reactant 3

HCID 10340Sodium CarbonateHCID 922693-Aminophenylboronic acidHCID 6138834-Iodo-3,5-dimethyl-1,2-oxazole

Product 1

HCID 116870263-(3,5-Dimethyl-isoxazol-4-yl)-phenylamineYield 85%

Reagents, catalysts & solvents 3

HCID 11979704Tetrakis(triphenylphosphine)palladiumCatalyst2×HCID 962WaterSolvent2×HCID 80711,2-DimethoxyethaneSolvent

Procedure

To a solution of 4-iodo-3,5-dimethylisoxazole (for a preparation see intermediate 1, 142 g, 640 mmol, 1 eq.) and (3-aminophenyl)boronic acid (100 g, 640 mmol, 1 eq.) in DME (600 ml) were added tetrakis(triphenylphosphine) palladium(0) (18.5 g, 16 mol) and a solution of Na2CO3 (203.5 g, 192 mmol, 3 eq.) in water (750 ml). The mixture was heated under reflux for 24 h. To complete the reaction intermediate 1 (0.2 eq.) and tetrakis(triphenylphosphine) palladium(0) (5 g) were added and the mixture was refluxed overnight. The cooled mixture was poured into water and extracted with DCM. The organic phase was washed with water, dried over Na2SO4 and filtered. Evaporation of the solvent in vacuo gave a crude oil which was precipitated with iPr2O to afford the title compound as a beige solid (102 g, 85%). [ES-MS] m/z: 189 MH+, Rt 2.20 min.

Workup

  1. temperatureThe mixture was heated
  2. temperatureunder reflux for 24 h
  3. additionwere added
  4. temperaturethe mixture was refluxed overnight
  5. extractionextracted with DCM
  6. washThe organic phase was washed with water
  7. dry with materialdried over Na2SO4
  8. filtrationfiltered
  9. customEvaporation of the solvent in vacuo
  10. customgave a crude oil which
  11. customwas precipitated with iPr2O

Sources & evidence

ORD record
ord-84354e46883840cbadc2e677d7c6d5fd
Source dataset
uspto-grants-2013_10
Patent number
US08557984B2

Reaction notes

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