Nitrogen → HCID 59300888, compound

HRID 2235400Notes

Reaction equation

HRID 2235400 reaction equation
[CH2:1]([N:5]1[C:13]2[CH:12]=[C:11]3[N:14]=[C:15]([C:17]4[CH:22]=[CH:21][C:20]([O:23][CH3:24])=[CH:19][CH:18]=4)[NH:16][C:10]3=[CH:9][C:8]=2[C:7]([CH3:26])([CH3:25])[C:6]1=O)[CH2:2][CH2:3][CH3:4].N#N.[H-].[H-].[H-].[H-].[Li+].[Al+3].[OH-].[Na+]>C1COCC1>[CH2:1]([N:5]1[C:13]2[CH:12]=[C:11]3[N:14]=[C:15]([C:17]4[CH:18]=[CH:19][C:20]([O:23][CH3:24])=[CH:21][CH:22]=4)[NH:16][C:10]3=[CH:9][C:8]=2[C:7]([CH3:25])([CH3:26])[CH2:6]1)[CH2:2][CH2:3][CH3:4]

Participants

6

Reactant 4

HCID 947NitrogenHCID 14798Sodium HydroxideHCID 21226445Aluminium lithium hydride2×HCID 59300951HCID 59300951, compound

Product 1

HCID 59300888HCID 59300888, compoundYield 97.1%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 5-butyl-2-(4-methoxy-phenyl)-7,7-dimethyl-5,7-dihydro-1H-imidazo[4,5-f]indol-6-one (150 mg) in dry THF (10 ml) under an inert atmosphere (N2) is added LiAlH4 (31.4 mg; 826 μmol). The reaction mixture is refluxed for 6 h and afterwards stirred at RT for another 15 h. Excess LiAlH4 is carefully hydrolyzed with NaOH solution (1 M; 30 ml). The aqueous layer is extracted with CH2Cl2 (3×30 ml). The combined organic layer is washed with brine, dried over MgSO4 and concentrated in vacuo to give the desired compound (140 mg).

Workup

  1. temperatureThe reaction mixture is refluxed for 6 h
  2. extractionThe aqueous layer is extracted with CH2Cl2 (3×30 ml)
  3. washThe combined organic layer is washed with brine
  4. dry with materialdried over MgSO4
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-d7daf38c555441a58071fcd1afd7acfe
Source dataset
uspto-grants-2010_05
Patent number
US07714010B2

Reaction notes

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