Water → 7-(3,4-dihydro-1H-isoquinolin-2-yl)-2,3-dimethyl-1H-pyrrolo[2,3-c]pyridin-5-carbaldehyde

HRID 1932399Notes

Reaction equation

HRID 1932399 reaction equation
[H-].C([Al+]CC(C)C)C(C)C.[CH2:11]1[C:20]2[C:15](=[CH:16][CH:17]=[CH:18][CH:19]=2)[CH2:14][CH2:13][N:12]1[C:21]1[N:22]=[C:23]([C:32]#N)[CH:24]=[C:25]2[C:29]([CH3:30])=[C:28]([CH3:31])[NH:27][C:26]=12.[OH2:34].[OH-].[Na+]>O1CCCC1.C(OCC)C>[CH2:11]1[C:20]2[C:15](=[CH:16][CH:17]=[CH:18][CH:19]=2)[CH2:14][CH2:13][N:12]1[C:21]1[N:22]=[C:23]([CH:32]=[O:34])[CH:24]=[C:25]2[C:29]([CH3:30])=[C:28]([CH3:31])[NH:27][C:26]=12

Participants

7

Reactant 4

HCID 962WaterHCID 14798Sodium HydroxideHCID 21225700DiisobutylaluminumhydrideHCID 67141782HCID 67141782, compound

Product 1

HCID 866152637-(3,4-dihydro-1H-isoquinolin-2-yl)-2,3-dimethyl-1H-pyrrolo[2,3-c]pyridin-5-carbaldehydeYield 16%

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 8028TetrahydrofuranSolvent

Procedure

Diisobutyl aluminum hydride (1.0M in toluene solution; 1.98 ml, 1.98 mmol) was added at −78° C. to a solution of 7-(3,4-dihydro-1H-isoquinolin-2-yl)-2,3-dimethyl-1H-pyrrolo[2,3-c]pyridin-5-carbonitrile (300 mg, 099 mmol) prepared in Example 682 in anhydrous tetrahydrofuran (2 ml). The reaction mixture was stirred for 5 hours and then diluted with diethyl ether. Water (2 ml) and 15% sodium hydroxide solution (2 ml) were added to the reaction mixture, which was then stirred for 30 minutes. The organic layer was dried on anhydrous magnesium sulfate and then concentrated under reduced pressure. The resulting residue was purified with silica gel column chromatography (ethyl acetate/n-hexane=1/3, v/v) to give 50.6 mg of the titled compound as a white solid. (Yield: 16%).

Workup

  1. stirringwas then stirred for 30 minutes
  2. dry with materialThe organic layer was dried on anhydrous magnesium sulfate
  3. concentrationconcentrated under reduced pressure
  4. customThe resulting residue was purified with silica gel column chromatography (ethyl acetate/n-hexane=1/3

Sources & evidence

ORD record
ord-7dbb6da45a164d0aa59ed777b1cd8430
Source dataset
uspto-grants-2012_05
Patent number
US08188114B2

Reaction notes

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