Potassium Carbonate → Methyl 2,4-dichloro-5-(3-fluoropyridin-2-yl)benzoate

HRID 522145Notes

Reaction equation

HRID 522145 reaction equation
[Cl:1][C:2]1[CH:11]=[C:10]([Cl:12])[C:9](B2OC(C)(C)C(C)(C)O2)=[CH:8][C:3]=1[C:4]([O:6][CH3:7])=[O:5].C(=O)([O-])[O-].[K+].[K+].Br[C:29]1[C:34]([F:35])=[CH:33][CH:32]=[CH:31][N:30]=1>C1COCC1.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:1][C:2]1[CH:11]=[C:10]([Cl:12])[C:9]([C:29]2[C:34]([F:35])=[CH:33][CH:32]=[CH:31][N:30]=2)=[CH:8][C:3]=1[C:4]([O:6][CH3:7])=[O:5]

Participants

7

Reactant 3

HCID 11430Potassium CarbonateHCID 27628032-Bromo-3-fluoropyridineHCID 68413491Methyl 2,4-dichloro-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzoate

Product 1

HCID 118497135Methyl 2,4-dichloro-5-(3-fluoropyridin-2-yl)benzoate

Reagents, catalysts & solvents 3

HCID 178418397HCID 178418397, compoundCatalystHCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of methyl 2,4-dichloro-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzoate (1.95 mol) in THF (4 L), was added portionwise a solution of potassium carbonate (807 g, 5.85 mol) in water (1.6 L), followed by 2-bromo-3-fluoropyridine (361 g, 2.05 mol) and the mixture degassed with argon. To this mixture was added tetrakis(triphenylphosphine)palladium (56.4 g, 48.8 mmol) and the mixture heated at reflux for 5 h. The mixture was cooled to room temperature and the organic layer separated and washed with brine (1 L). This organic solution containing the title compound was used directly in the next reaction (Preparation 27A).

Workup

  1. customthe mixture degassed with argon
  2. temperaturethe mixture heated
  3. temperatureat reflux for 5 h
  4. customthe organic layer separated
  5. washwashed with brine (1 L)
  6. additionThis organic solution containing the title compound
  7. customwas used directly in the next reaction (Preparation 27A)

Sources & evidence

ORD record
ord-5c4f0d39f5eb449996215a1f9a08d939
Source dataset
uspto-grants-2016_05
Patent number
US09328096B2

Reaction notes

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