Toluene → HCID 178520033, compound

HRID 1749864Notes

Reaction equation

HRID 1749864 reaction equation
[F:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[NH:7][N:6]=[C:5]2[C:11](OC)=[O:12].[H-].C([Al+]CC(C)C)C(C)C.C1(C)C=CC=CC=1.S([O-])([O-])(=O)=O.[Na+].[Na+]>C1COCC1>[F:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[NH:7][N:6]=[C:5]2[CH2:11][OH:12]

Participants

6

Reactant 4

HCID 1140TolueneHCID 24436Sodium SulfateHCID 12689297Methyl 5-fluoro-1H-indazole-3-carboxylateHCID 21225700Diisobutylaluminumhydride

Product 1

HCID 178520033HCID 178520033, compoundYield 43.5%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
-10 °C

Procedure

A solution of methyl 5-fluoro-1H-indazole-3-carboxylate (0.582 g, 3.00 mmol) in THF (20 mL) was cooled to −10° C., and added dropwise with a 1 M solution of diisobutylaluminum hydride in toluene (10.8 mL, 10.8 mmol) over 5 minutes. The reaction mixture was stirred at −10° C. for 1 hour, and then 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 (5-fluoro-1H-indazol-3-yl)methanol (0.217 g, 43%).

Workup

  1. customovernight
  2. customat room temperature
  3. customto terminate
  4. customthe reaction
  5. filtrationfiltered through Celite
  6. concentrationThe filtrate was concentrated
  7. customthe resulting residue was purified by silica gel column chromatography (chloroform/methanol)

Sources & evidence

ORD record
ord-fe148362102f482198a9d6b31a2bcc5c
Source dataset
uspto-grants-2015_10
Patent number
US09156827B2

Reaction notes

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