Dimethylformamide → HCID 59389386, compound

HRID 2357932Notes

Reaction equation

HRID 2357932 reaction equation
[Br:1][C:2]1[C:3]([C:10]#[C:11][CH:12]([CH3:14])[CH3:13])=[N:4][C:5]([O:8][CH3:9])=[CH:6][CH:7]=1.C[N:16](C=O)C.C(=O)([O-])[O-].[K+].[K+]>C(Cl)Cl.[Cl-].[Na+].O>[Br:1][C:2]1[C:3]2[N:4]([N:16]=[C:11]([CH:12]([CH3:14])[CH3:13])[CH:10]=2)[C:5]([O:8][CH3:9])=[CH:6][CH:7]=1

Participants

6

Reactant 3

HCID 6228DimethylformamideHCID 11430Potassium CarbonateHCID 593892733-Bromo-6-methoxy-2-(3-methyl-1-butyn-1-yl)pyridine

Product 1

HCID 59389386HCID 59389386, compound

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 57417360Sodium chloride; waterSolvent

Procedure

The compound of Example 261 (28.9 g) was added to a solution of MSH (26.1 g) in methylene chloride (250 mL) and the mixture was stirred for 4 hours, followed by concentration of the solvent and sequential addition of DMF (250 mL) and potassium carbonate (65.1 g). The resulting mixture was vigorously stirred at room temperature for 2 hours. Subsequently, saturated brine was added and the mixture was extracted with ether. The organic layer was dried over magnesium sulfate. The solvent was evaporated and the residue was purified by silica gel column chromatography (10 to 30% methylene chloride/petroleum ether). The purified product was solidified in petroleum ether to afford the title compound as a colorless powder (5.14 g).

Workup

  1. stirringThe resulting mixture was vigorously stirred at room temperature for 2 hours
  2. extractionthe mixture was extracted with ether
  3. dry with materialThe organic layer was dried over magnesium sulfate
  4. customThe solvent was evaporated
  5. customthe residue was purified by silica gel column chromatography (10 to 30% methylene chloride/petroleum ether)

Sources & evidence

ORD record
ord-ac9d2fe69eae49f5813a97424177cb32
Source dataset
uspto-grants-2010_07
Patent number
US07763617B2

Reaction notes

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