Cesium carbonate → Methyl 2-chloro-6-phenylpyridine-4-carboxylate

HRID 1096962Notes

Reaction equation

HRID 1096962 reaction equation
[C:1]1(B(O)O)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[C:10](=O)([O-])[O-].[Cs+].[Cs+].[Cl:16][C:17]1[CH:22]=[C:21]([C:23]([OH:25])=[O:24])[CH:20]=[C:19](Cl)[N:18]=1>Cl[Pd](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1.C1COCC1>[Cl:16][C:17]1[CH:22]=[C:21]([C:23]([O:25][CH3:10])=[O:24])[CH:20]=[C:19]([C:1]2[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=2)[N:18]=1

Participants

6

Reactant 3

HCID 10796Cesium carbonateHCID 66827Phenylboronic AcidHCID 948302,6-Dichloroisonicotinic acid

Product 1

HCID 53485792Methyl 2-chloro-6-phenylpyridine-4-carboxylate

Reagents, catalysts & solvents 2

HCID 178418476HCID 178418476, compoundCatalystHCID 8028TetrahydrofuranSolvent

Procedure

Phenylboronic acid (326 mg), PdCl2(PPh3)2 (84 mg) and cesium carbonate (3.9 g) were added in that order to a THF (10 mL) solution of 2,6-dichloropyridine-4-carboxylic acid (500 mg), and stirred under heat with refluxing for 1.5 hours. The reaction liquid was filtered through Celite, concentrated under reduced pressure, and the residue was purified through silica gel column chromatography (hexane/ethyl acetate) to obtain a crude product of the title compound as a yellow oil. Not purified, this was used in the next step.

Workup

  1. temperatureunder heat
  2. temperaturewith refluxing for 1.5 hours
  3. customThe reaction liquid
  4. filtrationwas filtered through Celite
  5. concentrationconcentrated under reduced pressure
  6. customthe residue was purified through silica gel column chromatography (hexane/ethyl acetate)

Sources & evidence

ORD record
ord-267175a88285425692536c261fc80bcb
Source dataset
uspto-grants-2012_03
Patent number
US08138197B2

Reaction notes

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