Aluminium lithium hydride → HCID 21964288, compound

HRID 2373471Notes

Reaction equation

HRID 2373471 reaction equation
[H-].[Al+3].[Li+].[H-].[H-].[H-].[CH3:7][C:8]1[CH:39]=[CH:38][C:11]([CH2:12][N:13]2[C:21]3[C:16](=[CH:17][C:18]([C:22]4[CH:27]=[CH:26][C:25]([O:28][C:29]([F:32])([F:31])[F:30])=[CH:24][CH:23]=4)=[CH:19][CH:20]=3)[CH:15]=[C:14]2[C:33](OCC)=[O:34])=[CH:10][CH:9]=1>C(OCC)C>[CH3:7][C:8]1[CH:9]=[CH:10][C:11]([CH2:12][N:13]2[C:21]3[C:16](=[CH:17][C:18]([C:22]4[CH:27]=[CH:26][C:25]([O:28][C:29]([F:31])([F:32])[F:30])=[CH:24][CH:23]=4)=[CH:19][CH:20]=3)[CH:15]=[C:14]2[CH2:33][OH:34])=[CH:38][CH:39]=1

Participants

4

Reactant 2

HCID 21226445Aluminium lithium hydrideHCID 21964300HCID 21964300, compound

Product 1

HCID 21964288HCID 21964288, compoundYield 86.2%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

Lithium aluminum hydride (0.244 g, 6.1 mmol) was added portionwise to a stirring solution of ethyl 1-(4-methylbenzyl)-5-[4-(trifluoromethoxy)phenyl]-1H-indole-2-carboxylate (2.0 g, 4.4 mmol) in ethyl ether (17 mL) at 0° C. under a nitrogen atmosphere over a period of 5 minutes. The mixture was then warmed up to room temperature. After the reaction mixture was stirred at room temperature for 5 hours, the reaction was carefully quenched with water and filtered. The filtrate was extracted with ethyl acetate. The organic extract was washed with water and brine, dried over anhydrous magnesium sulfate and evaporated to afford the title compound as a white solid (1.56 g, 86%). Mass spectrum (ESI, [M+H]+) m/z 412. 1HNMR (400 MHz, DMSO-d6): δ 7.81 (s, 1H), 7.76 (d, 2H, J=6.71 Hz), 7.45-7.35 (m, 4H), 7.08 (d, 2H, J=7.74 Hz), 6.96 (d, 2H, J=8.09 Hz), 6.50 (s, 1H), 5.44 (s, 2H), 5.35 (t, 1H), 4.60 (d, 2H), and 2.23 ppm (t, 3H).

Workup

  1. customthe reaction was carefully quenched with water
  2. filtrationfiltered
  3. extractionThe filtrate was extracted with ethyl acetate
  4. extractionThe organic extract
  5. washwas washed with water and brine
  6. dry with materialdried over anhydrous magnesium sulfate
  7. customevaporated

Sources & evidence

ORD record
ord-c71b8c5b315846d3ab10f10199fe98e9
Source dataset
uspto-grants-2008_12
Patent number
US07459478B2

Reaction notes

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