Sodium Carbonate → HCID 83816695, compound

HRID 1626513Notes

Reaction equation

HRID 1626513 reaction equation
Cl[C:2]1[CH:9]=[CH:8][C:5]([CH:6]=[O:7])=[C:4]([O:10][CH3:11])[N:3]=1.[CH:12]1(B(O)O)[CH2:14][CH2:13]1.C(=O)([O-])[O-].[Na+].[Na+]>C1(C)C=CC=CC=1.O.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd]>[CH:12]1([C:2]2[CH:9]=[CH:8][C:5]([CH:6]=[O:7])=[C:4]([O:10][CH3:11])[N:3]=2)[CH2:14][CH2:13]1

Participants

7

Reactant 3

HCID 10340Sodium CarbonateHCID 2760897Cyclopropylboronic acidHCID 108559456-Chloro-2-methoxypyridine-3-carbaldehyde

Product 1

HCID 83816695HCID 83816695, compoundYield 58.6%

Reagents, catalysts & solvents 3

HCID 9811564Bis(dibenzylideneacetone)palladiumCatalystHCID 962WaterSolventHCID 1140TolueneSolvent

Conditions

Temperature
90 °C

Procedure

6-Chloro-2-methoxynicotinaldehyde (200 mg, 1.17 mmol), cyclopropylboronic acid (200 mg, 2.33 mmol), sodium carbonate (371 mg, 3.50 mmol) and tetrakis(triphenylphosphine)palladium (0) (67.3 mg, 0.0583 mmol) were combined, diluted with toluene (2 mL) and water (200 μL). The reaction vial was purged with argon, heated to 90° C. and stirred for 12 hours. The reaction was cooled, loaded onto silica gel and eluted with 5% ethyl acetate/hexanes to 50% ethyl acetate/hexanes to yield 6-cyclopropyl-2-methoxynicotinaldehyde (121 mg, 0.683 mmol, 58.6% yield).

Workup

  1. customThe reaction
  2. customvial was purged with argon
  3. temperatureThe reaction was cooled
  4. washeluted with 5% ethyl acetate/hexanes to 50% ethyl acetate/hexanes

Sources & evidence

ORD record
ord-1f48e00462e0466192a67ab55b345afe
Source dataset
uspto-grants-2014_07
Patent number
US08785445B2

Reaction notes

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