Aluminium lithium hydride → HCID 15979849, compound

HRID 1866798Notes

Reaction equation

HRID 1866798 reaction equation
[NH:1]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[C:3]([S:10][C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=2[CH2:17][C:18]([N:20]([CH3:22])[CH3:21])=O)=[CH:2]1.[H-].[H-].[H-].[H-].[Li+].[Al+3]>C1COCC1>[NH:1]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[C:3]([S:10][C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=2[CH2:17][CH2:18][N:20]([CH3:21])[CH3:22])=[CH:2]1

Participants

4

Reactant 2

HCID 21226445Aluminium lithium hydrideHCID 57461321HCID 57461321, compound

Product 1

HCID 15979849HCID 15979849, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
50 °C

Procedure

2-[2-(1H-Indol-3-ylsulfanyl)-phenyl]-N,N-dimethyl-acetamide (116 mg, 0.37 mmol) in 6 mL THF is added to LiAlH4 (43 mg, 1.12 mmol) in 4 mL THF. The reaction mixture is stirred 16 hours at 50° C. The reaction is quenched with water and 2N NaOH. The reaction mixture is stirred for 1 hour, then 2.5 mL water is added and stirring was continued for another hour. The mixture is filtered, dried with MgSO4 and concentrated in vacuo. Purification by flash chromatography or preparative HPLC to gives the title compound. The following compounds were prepared analogously:

Workup

  1. customThe reaction is quenched with water and 2N NaOH
  2. stirringThe reaction mixture is stirred for 1 hour
  3. addition2.5 mL water is added
  4. stirringstirring
  5. waitwas continued for another hour
  6. filtrationThe mixture is filtered
  7. dry with materialdried with MgSO4
  8. concentrationconcentrated in vacuo
  9. customPurification by flash chromatography or preparative HPLC

Sources & evidence

ORD record
ord-4bc49d8ae39a434087ca6c32f587df9b
Source dataset
uspto-grants-2009_12
Patent number
US07629473B2

Reaction notes

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