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0 °C

To a cooled (0° C.) solution of 6-(thiazolo[4,5-b]pyridin-2-yloxy)-benzofuran-2-carboxylic acid methyl ester (6.0 g, 18.3 mmol) in DCM (183 mL) was added DIBALH (1 M in THF, 54.8 mL, 54.8 g, 54.8 mmol) and the reaction mixture was stirred (0° C., 1 h). The reaction mixture was treated with saturated aqueous Rochelle's salt (100 mL) and partitioned with DCM (50 mL). The organic layer was separated and the aqueous layer was extracted with DCM (2×100 mL). The organic layer was dried, filtered and concentrated in vacuo to provide the title compound as yellow solid (4.9 g, 90%). MS (ESI): mass calcd. for C16H10N2O3S, 298.04; m/z found, 299.0 [M+H]+. 1H NMR (500 MHz, DMSO-d6): 8.53 (dd, J=4.8, 1.7, 1H), 8.40 (dd, J=8.0, 1.7, 1H), 8.00 (s, 1H), 7.86 (d, J=2.1, 1H), 7.84 (s, 1H), 7.45-7.37 (m, 1H), 7.38-7.31 (m, 1H), 5.25 (t, J=5.5, 1H), 4.67 (dd, J=5.5, 0.8, 2H).

1. custompartitioned with DCM (50 mL)
2. customThe organic layer was separated
3. extractionthe aqueous layer was extracted with DCM (2×100 mL)
4. customThe organic layer was dried
5. filtrationfiltered
6. concentrationconcentrated in vacuo