Aluminium lithium hydride → HCID 24960188, compound

HRID 244404Notes

Reaction equation

HRID 244404 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]([NH:17]/[C:18](/[C:26]([F:29])([F:28])[F:27])=[CH:19]/[C:20]4[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=4)=[CH:14][CH:15]=3)[CH:10]=[N:9]2)=[CH:4][CH:3]=1.[H-].[Al+3].[Li+].[H-].[H-].[H-]>C1COCC1>[CH2:19]([CH:18]([NH:17][C:13]1[CH:12]=[C:11]2[C:16](=[CH:15][CH:14]=1)[N:8]([C:5]1[CH:4]=[CH:3][C:2]([F:1])=[CH:7][CH:6]=1)[N:9]=[CH:10]2)[C:26]([F:29])([F:27])[F:28])[C:20]1[CH:21]=[CH:22][CH:23]=[CH:24][CH:25]=1

Participants

4

Reactant 2

HCID 21226445Aluminium lithium hydrideHCID 59437282HCID 59437282, compound

Product 1

HCID 24960188HCID 24960188, compoundYield 14.7%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 66 mg (0.17 mmol) of [1-(4-fluorophenyl)-1H-indazol-5-yl]-((E)-2-phenyl-1-trifluoromethylvinyl)amine in THF was added 10 mg (0.26 mmol) of lithium aluminum hydride. The mixture stirred for 2 hours at room temperature and was then quenched with saturated aqueous sodium sulfate and extracted with EtOAc. The organic layer was washed with brine, dried over sodium sulfate and concentrated. The crude was purified by prep. TLC using 100% dichloromethane to provide 10 mg (7%) of the title compound as a yellow solid. MS m/z 400 (MH+).

Workup

  1. customwas then quenched with saturated aqueous sodium sulfate
  2. extractionextracted with EtOAc
  3. washThe organic layer was washed with brine
  4. dry with materialdried over sodium sulfate
  5. concentrationconcentrated
  6. customThe crude was purified by prep

Sources & evidence

ORD record
ord-ea072350e48740f49fb00c3f87eadf5d
Source dataset
uspto-grants-2014_02
Patent number
US08658637B2

Reaction notes

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