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Sodium hydride → 6,7-Dimethoxy-1-(3-methylsulfanyl-benzoyl)-isoquinoline-4-carbonitrile

HRID 1833240
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Reaction equation

HRID 1833240 reaction equation
Br[C:2]1[C:11]2[C:6](=[CH:7][C:8]([O:14][CH3:15])=[C:9]([O:12][CH3:13])[CH:10]=2)[C:5]([C:16]#[N:17])=[CH:4][N:3]=1.[CH3:18][S:19][C:20]1[CH:21]=[C:22]([CH:25]=[CH:26][CH:27]=1)[CH:23]=[O:24].[I-].C[NH+]1C=CN(C)C1.[H-].[Na+]>CN(C)C=O.C(OCC)(=O)C.CCCCCC.O>[CH3:15][O:14][C:8]1[CH:7]=[C:6]2[C:11](=[CH:10][C:9]=1[O:12][CH3:13])[C:2]([C:23](=[O:24])[C:22]1[CH:25]=[CH:26][CH:27]=[C:20]([S:19][CH3:18])[CH:21]=1)=[N:3][CH:4]=[C:5]2[C:16]#[N:17]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

8

Reactant 4

HCID 24758Sodium hydrideHCID 127211713-(Methylsulfanyl)benzaldehydeHCID 220483501-Bromo-6,7-dimethoxyisoquinoline-4-carbonitrileHCID 236182761,3-Dimethyl-1H-imidazolium iodide

Product 1

HCID 220483856,7-Dimethoxy-1-(3-methylsulfanyl-benzoyl)-isoquinoline-4-carbonitrileYield 57%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6228DimethylformamideSolventHCID 21226206Ethyl acetate hexaneSolvent

Procedure

To a stirred solution of 1-bromo-6,7-dimethoxy-isoquinoline-4-carbonitrile (100 mg, 0.34 mmol), 3-methylsulfanyl-benzaldehyde (104 g, 0.68 mmol) and 1,3-dimethyl-1H-imidazolium iodide (153 mg, 0.68 mmol) in N,N-dimethylformamide (3 mL) was added sodium hydride (27.3 mg, 0.68 mmol). The mixture turned black instantly. The reaction mixture was stirred at room temperature for 1 h. Water was added and the aqueous phase was extracted with dichloromethane (3×20 mL). The combined extracts were washed with saturated sodium chloride solution (20 mL), dried over anhydrous magnesium sulfate, filtered and concentrated in vacuo. Flash chromatography (Merck Silica gel 60, 70–230 mesh, 20% ethyl acetate/hexane) afforded 6,7-dimethoxy-1-(3-methylsulfanyl-benzoyl)-isoquinoline-4-carbonitrile (70 mg, 57% yield) as a colorless oil.

Workup

  1. extractionthe aqueous phase was extracted with dichloromethane (3×20 mL)
  2. washThe combined extracts were washed with saturated sodium chloride solution (20 mL)
  3. dry with materialdried over anhydrous magnesium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-12534dc908594ef2922d0d36e08f2aea
Source dataset
uspto-grants-2006_06
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07067529B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes