C[O:2][C:3]([C:5]1[NH:6][C:7]2[C:12]([CH:13]=1)=[CH:11][CH:10]=[C:9]([O:14][C:15]1[S:16][C:17]3[C:18]([N:23]=1)=[N:19][CH:20]=[CH:21][CH:22]=3)[CH:8]=2)=O.CC(C[AlH]CC(C)C)C.[NH4+].[Cl-]>C(Cl)Cl>[S:16]1[C:17]2[C:18](=[N:19][CH:20]=[CH:21][CH:22]=2)[N:23]=[C:15]1[O:14][C:9]1[CH:8]=[C:7]2[C:12]([CH:13]=[C:5]([CH2:3][OH:2])[NH:6]2)=[CH:11][CH:10]=1To a cooled (0° C.) solution of 6-(thiazolo[4,5-b]pyridin-2-yloxy)-1H-indole-2-carboxylic acid methyl ester (1.0 g, 3.1 mmol) in DCM (30 mL) was added DIBALH (1 M in THF, 15.4 mL, 13.2 g, 15.4 mmol) and the reaction mixture was stirred (0° C., 2 h). The reaction mixture was treated with saturated aqueous NH4Cl (1 mL), partitioned with EtOAc (50 mL) and saturated aqueous Rochelle's salt (50 mL). The organic layer was separated and the aqueous layer was extracted with EtOAc (2×50 mL). The organic layer was dried, filtered and concentrated in vacuo. The resulting residue was purified by silica gel flash chromatography using MeOH (0.2 M NH3):DCM (0-15%) to provide the title compound as yellow solid (287 mg, 31%). MS (ESI): mass calcd. for C16H11N3O2S, 297.1; m/z found, 298.0 [M+H]+. 1H NMR (400 MHz, CDCl3/CD3OD 10:1): 8.49 (dd, J=4.9, 1.6, 1H), 7.99 (dd, J=7.9, 1.6, 1H), 7.53 (d, J=8.5, 1H), 7.43 (d, J=2.0, 1H), 7.20 (dd, J=7.9, 4.9, 1H), 6.99 (dd, J=8.5, 2.2, 1H), 6.36 (s, 1H), 4.77 (s, 2H).
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