Dimethylformamide → HCID 67430909, compound

HRID 1661138Notes

Reaction equation

HRID 1661138 reaction equation
Br[C:2]1[CH:3]=[N:4][CH:5]=[C:6]([CH:14]=1)[C:7]([O:9][C:10]([CH3:13])([CH3:12])[CH3:11])=[O:8].C(=O)([O-])[O-].[K+].[K+].[CH2:21]1[O:29][C:28]2[CH:27]=[CH:26][C:25](B(O)O)=[CH:24][C:23]=2[O:22]1.CN(C)C=O>[Pd].O>[CH2:21]1[O:29][C:28]2[CH:27]=[CH:26][C:25]([C:2]3[CH:3]=[N:4][CH:5]=[C:6]([CH:14]=3)[C:7]([O:9][C:10]([CH3:13])([CH3:12])[CH3:11])=[O:8])=[CH:24][C:23]=2[O:22]1

Participants

7

Reactant 4

HCID 6228DimethylformamideHCID 11430Potassium CarbonateHCID 2734371(2H-1,3-benzodioxol-5-yl)boronic acidHCID 18422124tert-Butyl 5-bromonicotinate

Product 1

HCID 67430909HCID 67430909, compoundYield 88.1%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 962WaterSolvent

Conditions

Temperature
90 °C

Procedure

In a flask was placed tert-butyl 5-bromonicotinate (1.00 g, 3.87 mmol), 10% w/w palladium on carbon (210 mg, ˜0.2 mmol Pd), potassium carbonate (1.10 g, 7.96 mmol), 3,4-methylenedioxy-phenyl boronic acid (0.96 g, 5.79 mmol), dimethylformamide (50 mL) and water (250 L). The flask was purged with nitrogen and then heated, with stirring, to 90° C. for 15 hr. The reaction mixture was allowed to cool, diluted with water (350 mL) and extracted with CH2Cl2 (4X). The combined extracts was washed with water, dried (MgSO4) and concentrated in vacuo. The crude residue was purified by flash chromatography on silica (gradient, CH2Cl2 to 50% ether/CH2Cl2) to provide an off-white solid (1.02 g, 88%).

Workup

  1. customIn a flask was placed
  2. customThe flask was purged with nitrogen
  3. temperatureheated
  4. temperatureto cool
  5. additiondiluted with water (350 mL)
  6. extractionextracted with CH2Cl2 (4X)
  7. washThe combined extracts was washed with water
  8. dry with materialdried (MgSO4)
  9. concentrationconcentrated in vacuo
  10. customThe crude residue was purified by flash chromatography on silica (gradient, CH2Cl2 to 50% ether/CH2Cl2)

Sources & evidence

ORD record
ord-bb91667b12d04c4e8eb42e3621febe7c
Source dataset
uspto-grants-2011_10
Patent number
US08030336B2

Reaction notes

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