Diethyl Ether → 2((1-(4-fluorophenyl)-1H-indazol-5-yl)(phenyl)methyl)pentan-1-amine

HRID 218148Notes

Reaction equation

HRID 218148 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]([CH:17]([C:25]4[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=4)[CH:18]([CH2:22][CH2:23][CH3:24])[C:19]([NH2:21])=O)=[CH:14][CH:15]=3)[CH:10]=[N:9]2)=[CH:4][CH:3]=1.[H-].[Al+3].[Li+].[H-].[H-].[H-].C(OCC)C>C1COCC1>[F:1][C:2]1[CH:3]=[CH:4][C:5]([N:8]2[C:16]3[C:11](=[CH:12][C:13]([CH:17]([C:25]4[CH:26]=[CH:27][CH:28]=[CH:29][CH:30]=4)[CH:18]([CH2:22][CH2:23][CH3:24])[CH2:19][NH2:21])=[CH:14][CH:15]=3)[CH:10]=[N:9]2)=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 3283Diethyl EtherHCID 21226445Aluminium lithium hydrideHCID 687051803-(1-(4-fluorophenyl)-1H-indazol-5-yl)-2-propyl-3-phenylpropanamide

Product 1

HCID 687049822((1-(4-fluorophenyl)-1H-indazol-5-yl)(phenyl)methyl)pentan-1-amineYield 94%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a stirred solution of the crude 3-(1-(4-fluorophenyl)-1H-indazol-5-yl)-2-propyl-3-phenylpropanamide in anhydrous THF (10 mL) was added 1.0M lithium aluminum hydride in diethyl ether (2.0 mL, 2.0 mmol) portionwise at RT under nitrogen. After stirring at RT for 24 hr, the mixture was carefully quenched with MeOH, poured into brine (100 mL), extracted with ethyl acetate (2×100 mL), dried (Na2SO4) and concentrated to give 45 mg (94% yield, 3 steps) of 2((1-(4-fluorophenyl)-1H-indazol-5-yl)(phenyl)methyl)pentan-1-amine.

Workup

  1. customthe mixture was carefully quenched with MeOH
  2. additionpoured into brine (100 mL)
  3. extractionextracted with ethyl acetate (2×100 mL)
  4. dry with materialdried (Na2SO4)
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-49f6a6da506d4fd3aa4e2a9faa47c625
Source dataset
uspto-grants-2012_06
Patent number
US08198311B2

Reaction notes

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