Sodium sulfate decahydrate → (5-bromo-2-methyl-2H-indazol-4-yl)methanol

HRID 1639797Notes

Reaction equation

HRID 1639797 reaction equation
[H-].[Al+3].[Li+].[H-].[H-].[H-].[Br:7][C:8]1[CH:16]=[CH:15][C:14]2[C:10](=[CH:11][N:12]([CH3:17])[N:13]=2)[C:9]=1[C:18](OC)=[O:19].O.O.O.O.O.O.O.O.O.O.S([O-])([O-])(=O)=O.[Na+].[Na+]>O1CCCC1>[Br:7][C:8]1[CH:16]=[CH:15][C:14]2[C:10](=[CH:11][N:12]([CH3:17])[N:13]=2)[C:9]=1[CH2:18][OH:19]

Participants

5

Reactant 3

HCID 62649Sodium sulfate decahydrateHCID 21226445Aluminium lithium hydrideHCID 59145918methyl 5-bromo-2-methyl-2H-indazole-4-carboxylate

Product 1

HCID 59334512(5-bromo-2-methyl-2H-indazol-4-yl)methanolYield 73%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a suspension of lithium aluminum hydride (152 mg, 4.00 mmol) in tetrahydrofuran (15 mL) was added a solution of methyl 5-bromo-2-methyl-2H-indazole-4-carboxylate (534 mg, 2.00 mmol) in tetrahydrofuran (5 mL) at 0° C., and the mixture was stirred at room temperature for 15 min. To the reaction solution was added sodium sulfate decahydrate (1.5 g), and the mixture was stirred for 15 min and filtered through celite. The filtrate was concentrated under reduced pressure and the residue was purified by silica gel column chromatography (ethyl acetate/hexane=40/60→80/20) to give the title compound (351 mg, yield 73%).

Workup

  1. stirringthe mixture was stirred for 15 min
  2. filtrationfiltered through celite
  3. concentrationThe filtrate was concentrated under reduced pressure
  4. customthe residue was purified by silica gel column chromatography (ethyl acetate/hexane=40/60→80/20)

Sources & evidence

ORD record
ord-55fcac7650814f979e8c801194a4034a
Source dataset
uspto-grants-2012_02
Patent number
US08110585B2

Reaction notes

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