Water → HCID 67141219, compound

HRID 1932421Notes

Reaction equation

HRID 1932421 reaction equation
[BH4-].[Na+].[CH2:3]([N:6]1[C:10]2=[C:11]([N:17]3[CH2:26][CH2:25][C:24]4[C:19](=[CH:20][CH:21]=[CH:22][CH:23]=4)[CH2:18]3)[N:12]=[C:13]([C:15]#[N:16])[CH:14]=[C:9]2[C:8]([CH:27]=[O:28])=[C:7]1[CH3:29])[CH:4]=[CH2:5].O>CO>[CH2:3]([N:6]1[C:10]2=[C:11]([N:17]3[CH2:26][CH2:25][C:24]4[C:19](=[CH:20][CH:21]=[CH:22][CH:23]=4)[CH2:18]3)[N:12]=[C:13]([C:15]#[N:16])[CH:14]=[C:9]2[C:8]([CH2:27][OH:28])=[C:7]1[CH3:29])[CH:4]=[CH2:5]

Participants

5

Reactant 3

HCID 962WaterHCID 4311764Sodium borohydrideHCID 86615277HCID 86615277, compound

Product 1

HCID 67141219HCID 67141219, compoundYield 28.5%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Sodium borohydride (111.2 mg, 2.94 mmol) was added to a solution of 1-allyl-7-(3,4-dihydro-1H-isoquinolin-2-yl)-3-formyl-2-methyl-1H-pyrrolo[2,3-c]pyridin-5-carbonitrile (350 mg, 0.98 mmol) prepared in Step 4 in methanol (10 ml). The reaction mixture was stirred for 1 hour. Water was added to the reaction mixture, which was then extracted with ethyl acetate. 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=1/1, v/v) to give 100 mg of the titled compound as a white solid.

Workup

  1. extractionwas then extracted with ethyl acetate
  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=1/1

Sources & evidence

ORD record
ord-756d1fa2190a419ebf8fcadd3aa0149d
Source dataset
uspto-grants-2012_05
Patent number
US08188114B2

Reaction notes

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