Methanol → HCID 68296435, compound

HRID 1778167Notes

Reaction equation

HRID 1778167 reaction equation
[NH:1]1[C:5]2=[N:6][CH:7]=[CH:8][CH:9]=[C:4]2[C:3]([C:10]2[C:18]3[C:13](=[CH:14][N:15]=[CH:16][CH:17]=3)[NH:12][CH:11]=2)=[CH:2]1.[H-].[Na+].[CH2:21](Br)[C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1.CO>CN(C=O)C>[CH2:21]([N:1]1[C:5]2=[N:6][CH:7]=[CH:8][CH:9]=[C:4]2[C:3]([C:10]2[C:18]3[C:13](=[CH:14][N:15]=[CH:16][CH:17]=3)[NH:12][CH:11]=2)=[CH:2]1)[C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1

Participants

6

Reactant 4

HCID 887MethanolHCID 7498Benzyl BromideHCID 24758Sodium hydrideHCID 59053717HCID 59053717, compound

Product 1

HCID 68296435HCID 68296435, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

60 mg (0.16 mmol) of 3-(1H-pyrrolo[2,3-b]pyridin-3-yl)-1H-pyrrolo[2,3-c]pyridine (“A18”) are added to a suspension, kept under argon, of 20 mg (0.5 mmol) of sodium hydride (60% in paraffin) in 1 ml of DMF. After stirring at room temperature for one hour, 25 μl (0.26 mmol) of benzyl bromide are added, and the mixture is stirred at room temperature for 19 hours. Methanol is added to the reaction mixture, which is subsequently evaporated, and the residue is chromatographed on a silica-gel column with dichloromethane/methanol as eluent: 3-(1-benzyl-1H-pyrrolo[2,3-b]pyridin-3-yl)-1H-pyrrolo[2,3-c]pyridine as colourless solid;

Workup

  1. stirringthe mixture is stirred at room temperature for 19 hours
  2. customis subsequently evaporated
  3. customthe residue is chromatographed on a silica-gel column with dichloromethane/methanol as eluent

Sources & evidence

ORD record
ord-31b4eaf6cf8a4fedb61da4c0892f3161
Source dataset
uspto-grants-2016_02
Patent number
US09266887B2

Reaction notes

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