Aluminium lithium hydride → 3-(5-Formylpyridin-2-yl)-2-hydroxy-1H-indole-5-carbonitrile

HRID 1881331Notes

Reaction equation

HRID 1881331 reaction equation
[C:1]([C:3]1[CH:4]=[C:5]2[C:9](=[CH:10][CH:11]=1)[NH:8][C:7]([OH:12])=[C:6]2[C:13]1[CH:24]=[CH:23][C:16]([C:17](N(OC)C)=[O:18])=[CH:15][N:14]=1)#[N:2].[H-].[H-].[H-].[H-].[Li+].[Al+3]>C1COCC1.C(OCC)(=O)C>[CH:17]([C:16]1[CH:23]=[CH:24][C:13]([C:6]2[C:5]3[C:9](=[CH:10][CH:11]=[C:3]([C:1]#[N:2])[CH:4]=3)[NH:8][C:7]=2[OH:12])=[N:14][CH:15]=1)=[O:18]

Participants

5

Reactant 2

HCID 21226445Aluminium lithium hydrideHCID 1362398576-(5-Cyano-2-hydroxy-1H-indol-3-yl)-N-methoxy-N-methylnicotinamide

Product 1

HCID 1362769533-(5-Formylpyridin-2-yl)-2-hydroxy-1H-indole-5-carbonitrileYield 68%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

To an icecold suspension of 50 mg (0.16 mmol) of 6-(5-cyano-2-hydroxy-1H-indol-3-yl)-N-methoxy-N-methylnicotin-amide from example 1.2 in THF (4 mL) were added 19.4 mg (0.51 mmol) of LiAlH4 as a solid in small portions. The resulting mixture was stirred at that temperature for further 30 min. After diluting with ethyl acetate the reaction was quenched by adding 4.2 mL of a 0.35 M solution of KHSO4. The resulting solution was stirred for further 60 min, the phases were separated, and the precipitate in the organic layer was collected by filtration, washed with water and ethyl acetate, and dried in a vacuum oven yielding a red solid. Amount 28 mg. Yield 68%.

Workup

  1. customwas quenched
  2. additionby adding 4.2 mL of a 0.35 M solution of KHSO4
  3. stirringThe resulting solution was stirred for further 60 min
  4. customthe phases were separated
  5. filtrationthe precipitate in the organic layer was collected by filtration
  6. washwashed with water and ethyl acetate
  7. customdried in a vacuum oven
  8. customyielding a red solid

Sources & evidence

ORD record
ord-2d0a549c23724f919c7253341a43d834
Source dataset
uspto-grants-2012_11
Patent number
US08318793B2

Reaction notes

Loading…