5-{[4-(tetrahydro-2H-pyran-2-yloxy)cyclohexyl]oxy}-1H-indazole → 4-(1H-indazol-5-yloxy)cyclohexanol

HRID 1269807Notes

Reaction equation

O1CCCCC1[O:7][CH:8]1[CH2:13][CH2:12][CH:11]([O:14][C:15]2[CH:16]=[C:17]3[C:21](=[CH:22][CH:23]=2)[NH:20][N:19]=[CH:18]3)[CH2:10][CH2:9]1>CO>[NH:20]1[C:21]2[C:17](=[CH:16][C:15]([O:14][CH:11]3[CH2:12][CH2:13][CH:8]([OH:7])[CH2:9][CH2:10]3)=[CH:23][CH:22]=2)[CH:18]=[N:19]1

Participants

Conditions

Temperature: 50 °C

Procedure

An acidic resin (Dowex 50W×8, trade name, Dow Chemical Company, 46 mg) was added to a solution of 5-{[4-(tetrahydro-2H-pyran-2-yloxy)cyclohexyl]oxy}-1H-indazole (232 mg, 0.733 mmol) in methanol (10 ml), and the resulting mixture was heated to 50° C. After 5 hours, the reaction solution was filtered by the use of Celite and the filtrate was concentrated under reduced pressure. The resulting residue was purified by a silica gel column chromatography (eluent: chloroform/methanol) to obtain 4-(1H-indazol-5-yloxy)cyclohexanol (132 g, 78%).

Workup

filtrationthe reaction solution was filtered by the use of Celite
concentrationthe filtrate was concentrated under reduced pressure
customThe resulting residue was purified by a silica gel column chromatography (eluent: chloroform/methanol)

Sources & evidence

ORD record: ord-97e04fa6ee9a4ae192ee2de1e19dc839
Source dataset: uspto-grants-2007_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07199147B2

Reaction notes

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