Diisobutylaluminum hydride → [6-(Thiazolo[4,5-b]pyridin-2-yloxy)-benzofuran-2-yl]-methanol
Reaction equation
C([O:3][C:4]([C:6]1[O:7][C:8]2[CH:14]=[C:13]([O:15][C:16]3[S:17][C:18]4[C:19]([N:24]=3)=[N:20][CH:21]=[CH:22][CH:23]=4)[CH:12]=[CH:11][C:9]=2[CH:10]=1)=O)C.CC(C[AlH]CC(C)C)C>C(Cl)Cl>[S:17]1[C:18]2[C:19](=[N:20][CH:21]=[CH:22][CH:23]=2)[N:24]=[C:16]1[O:15][C:13]1[CH:12]=[CH:11][C:9]2[CH:10]=[C:6]([CH2:4][OH:3])[O:7][C:8]=2[CH:14]=1Participants
4
Procedure
To a cooled (0° C.) solution 6-(thiazolo[4,5-b]pyridin-2-yloxy)-benzofuran-2-carboxylic acid ethyl ester (300 mg, 0.8 mmol) in DCM (8 mL) was added DIBALH (1 M in THF, 3 mL, 3 mmol) and the reaction mixture was warmed (rt, 48 h). The reaction mixture was quenched with saturated aqueous Rochelle's Salt (2 mL) and partitioned with DCM. The organic layer was separated and the aqueous layer was extracted with DCM (2×15 mL). The organic layers were combined, dried, filtered and concentrated in vacuo. The resulting residue was purified by silica gel flash chromatography using MeOH:DCM (0-10%) to provide the title compound as a yellow solid (197 mg, 82%). MS (ESI): mass calcd. for C16H10N2O3S, 298.1; m/z found, 299.1 [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), 7.84 (d, J=1.7, 1H), 7.74 (d, J=8.4, 1H), 7.44-7.26 (m, 2H), 6.86 (s, 1H), 5.54 (t, J=5.9, 1H), 4.60 (d, J=5.9, 2H).