[CH3:1][C:2]1[CH:7]=[C:6]([C:8]2[C:16]3[C:11](=[CH:12][CH:13]=[C:14]([C:17]([OH:19])=[O:18])[CH:15]=3)[N:10](C(C3C=CC=CC=3)(C3C=CC=CC=3)C3C=CC=CC=3)[N:9]=2)[CH:5]=[CH:4][N:3]=1.FC(F)(F)C(O)=O.C([SiH](CC)CC)C>ClCCl.Cl>[CH3:1][C:2]1[CH:7]=[C:6]([C:8]2[C:16]3[C:11](=[CH:12][CH:13]=[C:14]([C:17]([OH:19])=[O:18])[CH:15]=3)[NH:10][N:9]=2)[CH:5]=[CH:4][N:3]=1
The synthetic intermediate from Step 1 (392 mg, 0.791 mmol), dichloromethane (2 ml), and trifluoroacetic acid (2 ml) were combined in an open vial. Triethylsilane (1.011 ml, 6.33 mmol) was then added, and the resulting mixture was stirred at a temperature of 23° C. for 50 minutes. The reaction mixture was then diluted with dichloromethane, and 2N HCl was added drop-wise until the pH of the mixture was between 4 and 5. This resulting precipitate was collected via filtration and rinsed with water, methanol and dichloromethane to afford 3-(2-methylpyridin-4-yl)-1H-indazole-5-carboxylic acid (220 mg, 0.674 mmol, 85% yield) as a green solid. The crude product was progressed to the next step without purification.
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