Aluminium lithium hydride → HCID 21071568, compound

HRID 1371857Notes

Reaction equation

HRID 1371857 reaction equation
[H-].[H-].[H-].[H-].[Li+].[Al+3].[F:7][C:8]1[CH:13]=[CH:12][C:11]([C:14]2[CH:15]=[C:16]3[C:20](=[CH:21][CH:22]=2)[NH:19][CH:18]=[C:17]3[CH:23]=[CH:24][N+:25]([O-])=O)=[CH:10][CH:9]=1>C1COCC1>[F:7][C:8]1[CH:13]=[CH:12][C:11]([C:14]2[CH:15]=[C:16]3[C:20]([NH:19][CH:18]=[C:17]3[CH2:23][CH2:24][NH2:25])=[CH:21][CH:22]=2)=[CH:10][CH:9]=1

Participants

4

Reactant 2

HCID 21226445Aluminium lithium hydrideHCID 67442368HCID 67442368, compound

Product 1

HCID 21071568HCID 21071568, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

Combine LiAlH4 (2.66 g, 70.17 mmol) and dry THF (70.0 ml) and cool the suspension in an ice bath. Add dropwise a solution of 5-(4-fluorophenyl)-3-(2-nitrovinyl)-1H-indole (3.30 g, 11.69 mmol) in dry THF (30.0 ml). Heat to reflux. After 1 hour, cool to ambient temperature and stir. After 15 hours, quench with saturated Na2SO4 (100 ml/mol) and stir at ambient temperature. After 1 hour, filter, rinse the precipitate with THF, and evaporate the filtrate to residue. Chromatograph the residue on silica gel eluting with dichloromethane/2N NH3(methanol) (80/20) to give the title compound. Prepare the HCl salt in diethyl ether: mp>250° C. MS (ACPI): m/e 255.0 (M+1). Analysis for C16H16ClFN2: Calcd: C, 66.09; H, 5.55; N, 9.63; found: C, 65.78; H, 5.48; N, 9.58.

Workup

  1. temperatureHeat to reflux
  2. waitAfter 15 hours
  3. customquench with saturated Na2SO4 (100 ml/mol)
  4. stirringstir at ambient temperature
  5. waitAfter 1 hour
  6. filtrationfilter
  7. washrinse the precipitate with THF
  8. customevaporate the filtrate to residue

Sources & evidence

ORD record
ord-163763c15037496980450b45e01c3646
Source dataset
uspto-grants-2007_01
Patent number
US07157488B2

Reaction notes

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