Sodium Carbonate → HCID 57825688, compound

HRID 2089110Notes

Reaction equation

HRID 2089110 reaction equation
C([O-])([O-])=O.[Na+].[Na+].[CH:7]([C:9]1[CH:14]=[CH:13][C:12](B(O)O)=[CH:11][CH:10]=1)=[O:8].[Cl:18][C:19]1[C:20](Cl)=[N:21][CH:22]=[C:23]([CH:29]=1)[C:24]([NH:26][CH2:27][CH3:28])=[O:25]>COCCOC.O.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>[Cl:18][C:19]1[C:20]([C:12]2[CH:13]=[CH:14][C:9]([CH:7]=[O:8])=[CH:10][CH:11]=2)=[N:21][CH:22]=[C:23]([CH:29]=1)[C:24]([NH:26][CH2:27][CH3:28])=[O:25]

Participants

7

Reactant 3

HCID 10340Sodium CarbonateHCID 5910734-Formylphenylboronic AcidHCID 201201335,6-Dichloro-N-ethylnicotinamide

Product 1

HCID 57825688HCID 57825688, compoundYield 80.4%

Reagents, catalysts & solvents 3

HCID 178418397HCID 178418397, compoundCatalystHCID 962WaterSolventHCID 80711,2-DimethoxyethaneSolvent

Procedure

2.44 g of Na2CO3 (23.0 mmol), 1.15 g of 4-formylphenylboronic acid (7.67 mmol), and 0.21 g of Pd(PPh3)4 were added to 1.68 g of 5,6-dichloro-N-ethyl-nicotinamide (5) (7.67 mmol) prepared in Example 2 dissolved in 30 mL of 1,2-dimethoxyethane and 30 mL of distilled water, and refluxed under heating and stirring for 18 hours. The mixture was cooled to room temperature, concentrated about 50% under reduced pressure to extract the aqueous layer with ethyl acetate. The organic layer was dried over magnesium sulfate, and concentrated under reduced pressure. The residue was separated by column chromatography (eluting solvent: chloroform/methanol=10/1) to obtain 5-chloro-N-ethyl-6-(4-formyl-phenyl)-nicotinamide 1.78 g (yield 80%).

Workup

  1. temperatureunder heating
  2. concentrationconcentrated about 50% under reduced pressure
  3. extractionto extract the aqueous layer with ethyl acetate
  4. dry with materialThe organic layer was dried over magnesium sulfate
  5. concentrationconcentrated under reduced pressure
  6. customThe residue was separated by column chromatography (eluting solvent: chloroform/methanol=10/1)

Sources & evidence

ORD record
ord-7e9ae4a8a8964147832b502f4886abbc
Source dataset
uspto-grants-2013_05
Patent number
US08436022B2

Reaction notes

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