Methanol → HCID 59053716, compound

HRID 875047Notes

Reaction equation

HRID 875047 reaction equation
[NH:1]1[C:5]2=[N:6][CH:7]=[CH:8][CH:9]=[C:4]2[C:3]([C:10]2[CH:19]=[CH:18][CH:17]=[C:16]3[C:11]=2[CH:12]=[CH:13][N:14]=[CH:15]3)=[CH:2]1.[H-].[Na+].I[CH3:23].CO>CN(C=O)C>[CH3:23][N:1]1[C:5]2=[N:6][CH:7]=[CH:8][CH:9]=[C:4]2[C:3]([C:10]2[CH:19]=[CH:18][CH:17]=[C:16]3[C:11]=2[CH:12]=[CH:13][N:14]=[CH:15]3)=[CH:2]1

Participants

6

Reactant 4

HCID 887MethanolHCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 59053651HCID 59053651, compound

Product 1

HCID 59053716HCID 59053716, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

53 mg (0.216 mmol) of 5-(1H-pyrrolo[2,3-b]pyridin-3-yl)isoquinoline are added to a suspension, kept under an argon atmosphere, of 26 mg (0.65 mmol) of sodium hydride, (60% suspension in paraffin oil) in 1 ml of DMF, and the reaction mixture is stirred at room temperature for 1 hour. 18 μl (0.65 mmol) of iodomethane are then added, and the reaction mixture is stirred at room temperature for a further 17 hours. 0.5 ml of methanol is then added, and the reaction mixture is subsequently evaporated in vacuo. The residue is chromatographed on a silica-gel column with dichloromethane/methanol as eluent, giving 5-(1-methyl-1H-pyrrolo[2,3-b]pyridin-3-yl)isoquinoline as colourless solid; MS (EI): 259 [M]+;

Workup

  1. stirringthe reaction mixture is stirred at room temperature for a further 17 hours
  2. customthe reaction mixture is subsequently evaporated in vacuo
  3. customThe residue is chromatographed on a silica-gel column with dichloromethane/methanol as eluent

Sources & evidence

ORD record
ord-9d39ea7d1fcb44f3a9b6fd96706d603f
Source dataset
uspto-grants-2015_03
Patent number
US08981101B2

Reaction notes

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