Water → HCID 178519323, compound

HRID 878785Notes

Reaction equation

HRID 878785 reaction equation
[Cl:1][C:2]1[C:10]2[C:5](=[CH:6][C:7]([C:11](OC)=[O:12])=[CH:8][CH:9]=2)[NH:4][N:3]=1.[H-].C([Al+]CC(C)C)C(C)C.O>O1CCCC1>[Cl:1][C:2]1[C:10]2[C:5](=[CH:6][C:7]([CH2:11][OH:12])=[CH:8][CH:9]=2)[NH:4][N:3]=1

Participants

5

Reactant 3

HCID 962WaterHCID 21225700DiisobutylaluminumhydrideHCID 178497276HCID 178497276, compound

Product 1

HCID 178519323HCID 178519323, compoundYield 45%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of methyl 3-chloro-1H-indazole-6-carboxylate (891 mg, 4.2 mmol) in tetrahydrofuran (10 mL) was cooled to −78° C., and then thereto was added dropwise diisobutylaluminum hydride (tetrahydrofuran solution, 1 mol/L, 12.7 mL, 12.6 mmol) at the same temperature, and the mixture was stirred at the same temperature for 2 hours. To the reaction solution was added water, and the mixture was extracted with ethyl acetate twice. The organic layer was combined, washed with water and saturated brine, dried over anhydrous sodium sulfate, and then concentrated under reduced pressure. The resulting residue was purified by silica gel column chromatography hexane→hexane:ethyl acetate=2:1) to give (3-chloro-1H-indazol-6-yl)methanol (344 mg, 45%) as a yellow solid.

Workup

  1. extractionthe mixture was extracted with ethyl acetate twice
  2. washwashed with water and saturated brine
  3. dry with materialdried over anhydrous sodium sulfate
  4. concentrationconcentrated under reduced pressure
  5. customThe resulting residue was purified by silica gel column chromatography hexane→hexane

Sources & evidence

ORD record
ord-4d27e4b16b034f28886fb23ed065e381
Source dataset
uspto-grants-2015_03
Patent number
US08987445B2

Reaction notes

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