Water → 5-(4-Bromophenyl)-3-methylisoxazol-4-amine

HRID 1512547Notes

Reaction equation

HRID 1512547 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[O:12][N:11]=[C:10]([CH3:13])[C:9]=2C(O)=O)=[CH:4][CH:3]=1.C1(P([N:31]=[N+]=[N-])(C2C=CC=CC=2)=O)C=CC=CC=1.C(N(CC)CC)C.O>C1(C)C=CC=CC=1.C1COCC1>[Br:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[O:12][N:11]=[C:10]([CH3:13])[C:9]=2[NH2:31])=[CH:4][CH:3]=1

Participants

7

Reactant 4

HCID 962WaterHCID 8471TriethylamineHCID 199401P,P-Diphenylphosphinic azideHCID 566045595-(4-Bromophenyl)-3-methyl-1,2-oxazole-4-carboxylic acid

Product 1

HCID 582185375-(4-Bromophenyl)-3-methylisoxazol-4-amine

Reagents, catalysts & solvents 2

HCID 1140TolueneSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
120 °C

Procedure

5-(4-Bromo-phenyl)-3-methyl-isoxazole-4-carboxylic acid (1.1 g, 4.1 mmol), diphenylphosphoryl azide (1.2 mL, 4.3 mmol), and triethylamine (1.14 mL, 8.2 mmol) were combined in toluene and stirred at 120° C. for 25 minutes. After cooling to room temperature, H2O (2 mL) in THF (2 mL) was added and the reaction was stirred at 88° C. for 2 hours. The mixture was cooled to room temperature and extracted with EtOAc. The combined organic layers were concentrated to give the title compound.

Workup

  1. temperatureAfter cooling to room temperature
  2. stirringthe reaction was stirred at 88° C. for 2 hours
  3. temperatureThe mixture was cooled to room temperature
  4. extractionextracted with EtOAc
  5. concentrationThe combined organic layers were concentrated

Sources & evidence

ORD record
ord-7858ec41762b4157bc604b280bc671ec
Source dataset
uspto-grants-2012_07
Patent number
US08217066B2

Reaction notes

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