Aluminium lithium hydride → HCID 59239025, compound

HRID 2061002Notes

Reaction equation

HRID 2061002 reaction equation
[CH3:1][N:2]([CH3:38])[CH2:3][CH2:4][NH:5][C:6]([C:8]1[CH:9]=[C:10]2[C:18](=[CH:19][CH:20]=1)[NH:17][C:16]1[C:15]([O:21][CH3:22])=[C:14]3[NH:23][C:24]4[CH:25]=[CH:26][C:27]([C:30]([NH:32][CH2:33][CH2:34][N:35]([CH3:37])[CH3:36])=O)=[CH:28][C:29]=4[C:13]3=[CH:12][C:11]2=1)=O.[H-].[H-].[H-].[H-].[Li+].[Al+3]>C1COCC1>[CH3:22][O:21][C:15]1[C:14]2[NH:23][C:24]3[C:29](=[CH:28][C:27]([CH2:30][NH:32][CH2:33][CH2:34][N:35]([CH3:36])[CH3:37])=[CH:26][CH:25]=3)[C:13]=2[CH:12]=[C:11]2[C:10]3[CH:9]=[C:8]([CH2:6][NH:5][CH2:4][CH2:3][N:2]([CH3:1])[CH3:38])[CH:20]=[CH:19][C:18]=3[NH:17][C:16]=12

Participants

4

Reactant 2

HCID 21226445Aluminium lithium hydrideHCID 45139070HCID 45139070, compound

Product 1

HCID 59239025HCID 59239025, compoundYield 7.6%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of N2,N10-bis(2-(dimethylamino)ethyl)-6-methoxy-5,7-dihydroindolo[2,3-b]carbazole-2,10-dicarboxamide (0.49 g, 0.97 mmol) in THF (100 mL) at 0° C. was added LiAlH4 (0.784 g, 20.66 mmol) under Ar and heated to reflux. The reaction mixture was quenched by dropwise addition of water (2 mL). The solution was filtered, concentrated, and purified by flash chromatography to provide the title product (35.8 mg). 1H-NMR (DMSO-d6, 400 MHz) δ ppm 10.94 (s, 2H), 8.74 (s, 1H), 8.05 (s, 2H), 7.36-7.22 (m, 4H), 4.12-4.05 (m, 2H), 3.84 (s, 3H), 3.16 (d, J=4.4 Hz, 4H), 2.62 (t, J=6.4 Hz, 4H), 2.34 (t, J=6.4 Hz, 4H), 2.10 (s, 12H); MS (ESI) m/z 485.4 (M−H)−

Workup

  1. temperatureheated to reflux
  2. customThe reaction mixture was quenched by dropwise addition of water (2 mL)
  3. filtrationThe solution was filtered
  4. concentrationconcentrated
  5. custompurified by flash chromatography

Sources & evidence

ORD record
ord-6ca8b4415f4c476d80d1705f292ea8ed
Source dataset
uspto-grants-2012_10
Patent number
US08278341B2

Reaction notes

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