Diethyl Ether → 3-(1-(4-fluorophenyl)-1H-indazol-5-yl)-2,3-diphenylpropan-1-amine

HRID 218152Notes

Reaction equation

HRID 218152 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:28]4[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=4)[CH:18]([C:22]4[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=4)[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:28]4[CH:29]=[CH:30][CH:31]=[CH:32][CH:33]=4)[CH:18]([C:22]4[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=4)[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 687038113-(1-(4-fluorophenyl)-1H-indazol-5-yl)-2,3-diphenylpropanamide

Product 1

HCID 687029583-(1-(4-fluorophenyl)-1H-indazol-5-yl)-2,3-diphenylpropan-1-amineYield 65%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a stirred solution of the crude 3-(1-(4-fluorophenyl)-1H-indazol-5-yl)-2,3-diphenylpropanamide 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 50 mg (65% yield, 3 steps) of 3-(1-(4-fluorophenyl)-1H-indazol-5-yl)-2,3-diphenylpropan-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-2927f95d0ff849ceaa3eaa6d4911f67b
Source dataset
uspto-grants-2012_06
Patent number
US08198311B2

Reaction notes

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