Pyridine → HCID 57767014, compound

HRID 1670697Notes

Reaction equation

HRID 1670697 reaction equation
[H-].[Na+].C(#N)[CH:4]([CH2:6][C:7]#[N:8])O.Br[C:11]1[N:16]=[CH:15][C:14]([N:17]2[C:26]3[N:27]4[CH:33]=[C:32]([O:34][CH3:35])[CH:31]=[CH:30][C:28]4=[N:29][C:25]=3[C:24]3[C:19](=[CH:20][CH:21]=[CH:22][CH:23]=3)[C:18]2=[O:36])=[CH:13][CH:12]=1.[N:37]1C=CC=CC=1>>[C:7]([CH:6]([C:11]1[CH:12]=[CH:13][C:14]([N:17]2[C:26]3[N:27]4[CH:33]=[C:32]([O:34][CH3:35])[CH:31]=[CH:30][C:28]4=[N:29][C:25]=3[C:24]3[C:19](=[CH:20][CH:21]=[CH:22][CH:23]=3)[C:18]2=[O:36])=[CH:15][N:16]=1)[C:4]#[N:37])#[N:8]

Participants

5

Reactant 4

HCID 1049PyridineHCID 24758Sodium hydrideHCID 212535622-HydroxybutanedinitrileHCID 24771268HCID 24771268, compound

Product 1

HCID 57767014HCID 57767014, compoundYield 19%

Procedure

Sodium hydride (2.5 equiv., 0.950 mmol, 0.038 g (60%)) was added to a solution of malonitrile (1.2 equiv., 0.456 mmol, 0.030 g) in dry pyridine (1 ml) under Ar atmosphere. The catalyst—prepared as described above—was injected, and the mixture was stirred at room temperature for 5 min. 6-(6-Bromo-pyridin-3-yl)-9-methoxypyrido[2′,1′:2,3]imidazo[4,5-c]isoquinolin-5(6H)-one (39) (1.0 equiv., 0.380 mmol, 0.160 g) was then added and the reaction mixture was heated at 85° C. for 2 h. After destruction of the excess of sodium hydride with methanol, the solvent was concentrated under vacuum. The residue was purified by column chromatography (gradient elution: dichloromethane/methanol (7M NH3) 9:1→8:2) to give α-cyano-5-[5,6-dihydro-9-methoxy-5-oxo-pyrido[2′,1′:2,3]imidazo[4,5-c]isoquinolin-6-yl]-2-pyridineacetonitrile (52) (0.030 g, yield=19%, purity (LC)=99%).

Workup

  1. customThe catalyst—prepared
  2. temperaturethe reaction mixture was heated at 85° C. for 2 h
  3. customAfter destruction of the excess of sodium hydride with methanol
  4. concentrationthe solvent was concentrated under vacuum
  5. customThe residue was purified by column chromatography (gradient elution: dichloromethane/methanol (7M NH3) 9:1→8:2)

Sources & evidence

ORD record
ord-ba15b0ee57114d059f81c644e25c6fb7
Source dataset
uspto-grants-2011_08
Patent number
US07994187B2

Reaction notes

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