Sodium Hydroxide → 3-(1-(4-fluorophenyl)-1H-indazol-5-yl)-2,2,3-trimethylbutan-1-amine

HRID 218176Notes

Reaction equation

HRID 218176 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]2[C:16]3[C:11](=[CH:12][C:13]([C:17]([CH3:25])([CH3:24])[C:18]([CH3:23])([CH3:22])[C:19]([NH2:21])=O)=[CH:14][CH:15]=3)[CH:10]=[N:9]2)=[CH:4][CH:3]=1.[H-].[H-].[H-].[H-].[Li+].[Al+3].[OH-].[Na+]>C1COCC1>[F:1][C:2]1[CH:3]=[CH:4][C:5]([N:8]2[C:16]3[C:11](=[CH:12][C:13]([C:17]([CH3:25])([CH3:24])[C:18]([CH3:23])([CH3:22])[CH2:19][NH2:21])=[CH:14][CH:15]=3)[CH:10]=[N:9]2)=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 14798Sodium HydroxideHCID 21226445Aluminium lithium hydrideHCID 687047833-(1-(4-fluorophenyl)-1H-indazol-5-yl)-2,2,3-trimethylbutanamide

Product 1

HCID 687049513-(1-(4-fluorophenyl)-1H-indazol-5-yl)-2,2,3-trimethylbutan-1-amineYield 112.8%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a stirred solution of 3-(1-(4-fluorophenyl)-1H-indazol-5-yl)-2,2,3-trimethylbutanamide (159 mg, 0.47 mmol) in anhydrous THF (5 mL) was added a solution of LAH (1 M in diethylether, 1 mL, 1 mmol) under nitrogen at 0° C. The mixture was stirred at the same temperature for 1 hr and at rt for 22 hr. After an aqueous solution of sodium hydroxide (1 M, 10 mL) was added slowly, the mixture was stirred for 0.5 hr and filtered through a pad of celite that was then rinsed with dichloromethane. The filtrate was extracted with dichloromethane (4×10 mL). The combined extracts were dried (Na2SO4) and concentrated in vacuo to give 3-(1-(4-fluorophenyl)-1H-indazol-5-yl)-2,2,3-trimethylbutan-1-amine (173 mg; 0.53 mmol, 110% yield) as a yellow foam solid that was used as such without further purification.

Workup

  1. stirringthe mixture was stirred for 0.5 hr
  2. filtrationfiltered through a pad of celite that
  3. washwas then rinsed with dichloromethane
  4. extractionThe filtrate was extracted with dichloromethane (4×10 mL)
  5. dry with materialThe combined extracts were dried (Na2SO4)
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-26d9ff4b4a154fe6ade8dd49c23284e4
Source dataset
uspto-grants-2012_06
Patent number
US08198311B2

Reaction notes

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