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. 2018 Aug 28;61(18):8337–8352. doi: 10.1021/acs.jmedchem.8b00832

Scheme 5. Preparation of the 5-Methylisoxazole-3-carboxylic Acid 13.

Scheme 5

Reagents and conditions: (i) NBS, TFA, 0 °C, heat under reflux, 16 h; (ii) ArB(OH)2, aq. NaHCO3, DMF, Pd(Ph3P)2Cl2, 90 °C, 5 h (28%); (iii) (CF3SO2)2O, py., DCM, 0 °C to rt, 6 h (66%); (iv) 21, Pd(Ph3P)4, DMF, 90 °C, 3 h; (v) NaOH, MeOH, 0 °C, 1 h (65%).