Sodium Carbonate → HCID 86664401, compound

HRID 1626530Notes

Reaction equation

HRID 1626530 reaction equation
Cl[C:2]1[CH:9]=[CH:8][C:5]([CH:6]=[O:7])=[C:4]([N:10]([CH3:12])[CH3:11])[N:3]=1.C(=O)([O-])[O-].[Na+].[Na+].[CH:19]1(B(O)O)[CH2:21][CH2:20]1>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:19]1([C:2]2[CH:9]=[CH:8][C:5]([CH:6]=[O:7])=[C:4]([N:10]([CH3:12])[CH3:11])[N:3]=2)[CH2:21][CH2:20]1

Participants

7

Reactant 3

HCID 10340Sodium CarbonateHCID 2760897Cyclopropylboronic acidHCID 706995566-Chloro-2-(dimethylamino)pyridine-3-carbaldehyde

Product 1

HCID 86664401HCID 86664401, compoundYield 62.6%

Reagents, catalysts & solvents 3

HCID 9811564Bis(dibenzylideneacetone)palladiumCatalystHCID 962WaterSolventHCID 1140TolueneSolvent

Conditions

Temperature
90 °C

Procedure

6-chloro-2-(dimethylamino)nicotinaldehyde (155 mg, 0.840 mmol), sodium carbonate (267 mg, 2.52 mmol), cyclopropylboronic acid (108 mg, 1.26 mmol) and palladium tetrakis(triphenylphosphine) (0) (48.5 mg, 0.0420 mmol) were diluted with toluene (2 mL) and water (200 μL). The reaction was purged with argon, sealed and heated to 90° C. After stirring for 4 hours, the reaction was cooled, loaded onto silica gel and eluted with 5% ethyl acetate/hexanes to 75% ethyl acetate/hexanes to yield 6-cyclopropyl-2-(dimethylamino)nicotinaldehyde (100 mg, 0.526 mmol, 62.6% yield).

Workup

  1. customThe reaction was purged with argon
  2. customsealed
  3. temperaturethe reaction was cooled
  4. washeluted with 5% ethyl acetate/hexanes to 75% ethyl acetate/hexanes

Sources & evidence

ORD record
ord-47a6a10b68cf4be5a698e7b9b3b93662
Source dataset
uspto-grants-2014_07
Patent number
US08785445B2

Reaction notes

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