Potassium Carbonate → HCID 86642286, compound

HRID 1097246Notes

Reaction equation

HRID 1097246 reaction equation
Br[C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([CH2:8][N:9]2[CH2:14][CH2:13][CH2:12][CH2:11][CH2:10]2)[N:3]=1.[CH:15]([C:17]1[CH:22]=[CH:21][C:20](B(O)O)=[CH:19][CH:18]=1)=[O:16].C(=O)([O-])[O-].[K+].[K+]>C1(C)C=CC=CC=1.C(O)C.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[N:9]1([CH2:8][C:4]2[N:3]=[C:2]([C:20]3[CH:21]=[CH:22][C:17]([CH:15]=[O:16])=[CH:18][CH:19]=3)[CH:7]=[CH:6][CH:5]=2)[CH2:14][CH2:13][CH2:12][CH2:11][CH2:10]1

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 5910734-Formylphenylboronic AcidHCID 137845442-Bromo-6-piperidin-1-ylmethylpyridine

Product 1

HCID 86642286HCID 86642286, compoundYield 87.4%

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 21863594Toluene ethanolSolvent

Procedure

To a solution of 2-bromo-6-piperidin-1-ylmethyl-pyridine (example 5) (8.0 g, 31.4 mmol) and 4-formylphenylboronic acid (6.1 g, 40.8 mmol) in toluene/ethanol (4/1, 320 ml) was added an aqueous solution of 2M potassium carbonate. After 15 minutes stirring under a nitrogen atmosphere, tetrakis(triphenylphosphine)palladium(0) (1.2 g, 1.02 mmol) was added. After stirring for 17 h at 80° C. under a nitrogen atmosphere, the mixture was cooled to room temperature and filtered through decalite. Water was added and the product was extracted into ethylacetate. The combined organic phases were washed with water, brine, dried over sodium sulfate and concentrated under reduced pressure. Column chromatography afforded 4-(6-(piperidin-1-ylmethyl)pyridin-2-yl)benzaldehyde (7.69 g) as a white solid.

Workup

  1. stirringAfter stirring for 17 h at 80° C. under a nitrogen atmosphere
  2. filtrationfiltered through decalite
  3. additionWater was added
  4. extractionthe product was extracted into ethylacetate
  5. washThe combined organic phases were washed with water, brine
  6. dry with materialdried over sodium sulfate
  7. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-4af48f05da004ddd90bddb18fe0f2f25
Source dataset
uspto-grants-2012_03
Patent number
US08143246B2

Reaction notes

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