[C:1]1([Mg]Br)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[CH3:9][C:10]1[N:11]=[C:12]([NH:15][C:16]2[CH:17]=[C:18]([CH:21]=[CH:22][N:23]=2)[CH:19]=[O:20])[S:13][CH:14]=1.C(OCC)(=O)C>CCOCC.C1COCC1>[CH3:9][C:10]1[N:11]=[C:12]([NH:15][C:16]2[CH:17]=[C:18]([CH:19]([C:1]3[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=3)[OH:20])[CH:21]=[CH:22][N:23]=2)[S:13][CH:14]=13.0 M Phenylmagnesium bromide (0.9982 mL, 2.995 mmol) in ether was added to THF (2 mL) at 0° C., and then 2-(4-methylthiazol-2-ylamino)isonicotinaldehyde (0.197 g, 0.8985 mmol) in THF (3 mL) was added. The reaction mixture was stirred for 30 minutes, then partitioned between saturated ammonium chloride and ethyl acetate. The organic layer was washed with brine, dried, and concentrated. The residue was purified via MPLC (Biotage) eluting with 2:3 hexane:ethyl acetate to afford (2-(4-methylthiazol-2-ylamino)pyridin-4-yl)(phenyl)methanol (0.107 g, 40.05% yield) as a white solid. 1H NMR (d6-DMSO) δ 11.10 (s, 1H), 8.14 (d, 1H), 7.24-7.37 (m, 5H), 7.11 (s, 1H), 6.81 (d, 1H), 6.50 (s, 1H), 6.09 (d, 1H), 5.64 (d, 1H), 2.22 (s, 3H).
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