Sodium Carbonate → HCID 73013037, compound

HRID 505959Notes

Reaction equation

HRID 505959 reaction equation
[CH3:1][O:2][C:3](=[O:12])[C:4]1[CH:9]=[C:8](Br)[C:7]([Cl:11])=[N:6][CH:5]=1.[Cl:13][C:14]1[CH:19]=[CH:18][C:17](B(O)O)=[CH:16][CH:15]=1.C(=O)([O-])[O-].[Na+].[Na+]>C1(C)C=CC=CC=1>[CH3:1][O:2][C:3](=[O:12])[C:4]1[CH:9]=[C:8]([C:17]2[CH:18]=[CH:19][C:14]([Cl:13])=[CH:15][CH:16]=2)[C:7]([Cl:11])=[N:6][CH:5]=1

Participants

5

Reactant 3

HCID 10340Sodium CarbonateHCID 742994-Chlorophenylboronic acidHCID 2764313Methyl 5-bromo-6-chloronicotinate

Product 1

HCID 73013037HCID 73013037, compoundYield 72%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
90 °C

Procedure

To a solution of 5-bromo-6-chloro-nicotinic acid methyl ester (10 g, 40 mmol) in toluene (200 mL) was added 4-chlorophenyl-boronic acid (6.4 g, 40 mmol), [1,1′-bis(diphenylphosphino)ferrrocene]dichlorpalladium(II) dichloromethane complex (1.6 g, 2 mmol) and 2 M sodiumcarbonate solution (60 mL). The reaction mixture was stirred for 2 h at 90° C. After cooling, the phases were separated; the aqueous phase was extracted once with ethyl acetate (200 mL), organic phases were washed once with water and brine (150 mL each), combined and dried over MgSO4. After evaporation of the solvent the crude product was purified by flash column chromatography (dichloromethane/heptane 2:1 to 9:1) to give 6-chloro-5-(4-chloro-phenyl)-nicotinic acid methyl ester as a colorless solid, 8.12 g (72% yield). m/z (ES+): 281.1, 283.1 (M+H).

Workup

  1. temperatureAfter cooling
  2. customthe phases were separated
  3. extractionthe aqueous phase was extracted once with ethyl acetate (200 mL), organic phases
  4. washwere washed once with water and brine (150 mL each)
  5. dry with materialdried over MgSO4
  6. customAfter evaporation of the solvent the crude product
  7. customwas purified by flash column chromatography (dichloromethane/heptane 2:1 to 9:1)

Sources & evidence

ORD record
ord-5eac30a0577245f489ef0e0aa32d2739
Source dataset
uspto-grants-2010_08
Patent number
US07781593B2

Reaction notes

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