Toluene → HCID 178520041, compound
Reaction equation
[F:1][C:2]([F:18])([F:17])[O:3][C:4]1[CH:5]=[C:6]2[C:10](=[CH:11][CH:12]=1)[NH:9][N:8]=[C:7]2[C:13](OC)=[O:14].[H-].C([Al+]CC(C)C)C(C)C.C1(C)C=CC=CC=1.S([O-])([O-])(=O)=O.[Na+].[Na+]>C1COCC1>[F:18][C:2]([F:1])([F:17])[O:3][C:4]1[CH:5]=[C:6]2[C:10](=[CH:11][CH:12]=1)[NH:9][N:8]=[C:7]2[CH2:13][OH:14]Participants
6
Conditions
- Temperature
- -10 °C
Procedure
A solution of methyl 5-(trifluoromethoxy)-1H-indazole-3-carboxylate (0.370 g, 1.42 mmol) in THF (10 mL) was cooled to −10° C., and added dropwise with a 1 M solution of diisobutylaluminum hydride in toluene (5.11 mL, 5.11 mmol) over 5 minutes. The reaction mixture was stirred at −10° C. for 1 hour, and then stirred overnight at room temperature. The reaction mixture was added dropwise with saturated aqueous sodium sulfate under ice cooling to terminate the reaction, and then filtered through Celite. The filtrate was concentrated, and the resulting residue was purified by silica gel column chromatography (chloroform/methanol) to obtain the objective [5-(trifluoromethoxy)-1H-indazol-3-yl]methanol (0.133 g, 40%).
Workup
- stirringstirred overnight at room temperature
- customto terminate
- customthe reaction
- filtrationfiltered through Celite
- concentrationThe filtrate was concentrated
- customthe resulting residue was purified by silica gel column chromatography (chloroform/methanol)
Sources & evidence
- ORD record
- ord-874533de0c984c8495edb7e23cabd2be
- Source dataset
- uspto-grants-2015_10
- Patent number
- US09156827B2
Reaction notes
Loading…