Cl.[CH2:2]([O:9][C:10]1[C:11]([NH:17][C:18]2[S:19][CH:20]=[C:21]([CH3:23])[N:22]=2)=[N:12][CH:13]=[C:14](Br)[CH:15]=1)[C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1.[Li]C.C([Li])CCC.C([O:34]B(OC(C)C)OC(C)C)(C)C.[OH-].[Na+].OO>CO.C1COCC1>[CH2:2]([O:9][C:10]1[CH:15]=[C:14]([OH:34])[CH:13]=[N:12][C:11]=1[NH:17][C:18]1[S:19][CH:20]=[C:21]([CH3:23])[N:22]=1)[C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1
3-(Benzyloxy)-5-bromo-N-(4-methylthiazol-2-yl)pyridin-2-amine (prepared according to Example 1; 1.00 g, 2.66 mmol) was added to THF (30 mL) and cooled to −78° C. MeLi (2.07 mL, 3.32 mmol) was slowly added, and the reaction mixture was stirred for 10 minutes. Butyllithium (1.33 mL, 3.32 mmol) was added, and the reaction mixture was stirred for 15 minutes. Triisopropylborate (0.613 mL, 2.66 mmol) was added, and the reaction mixture was stirred for 30 minutes. The reaction mixture was warmed to 0° C., and methanol (5 mL), 10% aqueous NaOH (5.1 mL, 12.8 mmol), and 30% aqueous H2O2 (1.27 mL, 13.3 mmol) were added. The reaction mixture was stirred at 0° C. for 1 hour, then purified by silica gel (10-20% EtOAc in hexanes) to give 5-(benzyloxy)-6-(4-methylthiazol-2-ylamino)pyridin-3-ol (0.198 g, 23.8% yield). 1H NMR (d6-DMSO) δ 7.59 (m, 3H), 7.40 (m, 3H), 7.17 (d, 1H), 6.84 (s, 1H), 5.31 (s, 2H), 2.33 (s, 3H). Mass spectrum (apci) m/z=314.1 (M+H).
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