[6-(Thiazolo[4,5-b]pyridin-2-yloxy)-1H-indol-2-yl]-methanol → 6-(Thiazolo[4,5-b]pyridin-2-yloxy)-1H-indole-2-carbaldehyde

HRID 1947463Notes

Reaction equation

[S:1]1[C:9]2[C:4](=[N:5][CH:6]=[CH:7][CH:8]=2)[N:3]=[C:2]1[O:10][C:11]1[CH:19]=[C:18]2[C:14]([CH:15]=[C:16]([CH2:20][OH:21])[NH:17]2)=[CH:13][CH:12]=1>C(Cl)(Cl)Cl.O=[Mn]=O>[S:1]1[C:9]2[C:4](=[N:5][CH:6]=[CH:7][CH:8]=2)[N:3]=[C:2]1[O:10][C:11]1[CH:19]=[C:18]2[C:14]([CH:15]=[C:16]([CH:20]=[O:21])[NH:17]2)=[CH:13][CH:12]=1

Participants

Conditions

Temperature: 80 °C

Procedure

To a solution of [6-(thiazolo[4,5-b]pyridin-2-yloxy)-1H-indol-2-yl]-methanol (0.89 g, 3.0 mmol) in CHCl3 (30 mL) was added MnO2 (2.6 g, 30 mmol) and the reaction mixture was heated (80° C., 3 h). The reaction mixture was cooled (rt), filtered (Celite®) and washed with isopropanol:DCM (15%, 300 mL). The filtrate was dried, filtered and concentrated in vacuo. The resulting residue was purified by reverse phase HPLC to provide the title compound as a colorless solid (139 mg, 16%). MS (ESI): mass calcd. for C16H9N3O2S, 295.0; m/z found, 296.0 [M+H]+. 1H NMR (400 MHz, DMSO-d6): 9.94 (s, 1H), 8.59 (dd, J=4.8, 1.7, 1H), 8.46 (dd, J=8.0, 1.7, 1H), 7.95 (t, J=18.7, 1H), 7.61 (d, J=2.2, 1H), 7.55 (s, 1H), 7.40 (dd, J=8.0, 4.8, 1H), 7.34-7.15 (m, 1H).

Workup

temperatureThe reaction mixture was cooled (rt)
filtrationfiltered (Celite®)
washwashed with isopropanol
customThe filtrate was dried
filtrationfiltered
concentrationconcentrated in vacuo
customThe resulting residue was purified by reverse phase HPLC

Sources & evidence

ORD record: ord-b7d05838e90c44df88987db468c14069
Source dataset: uspto-grants-2013_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08399465B2

Reaction notes

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