Potassium Carbonate → HCID 21942438, compound

HRID 2216770Notes

Reaction equation

HRID 2216770 reaction equation
C[O:2][C:3](=[O:12])[C:4]1[CH:9]=[C:8]([F:10])[CH:7]=[C:6](Br)[CH:5]=1.B1([C:19]2[CH:24]=[CH:23][CH:22]=[N:21][CH:20]=2)OCCCO1.C(=O)([O-])[O-].[K+].[K+]>C1(C)C=CC=CC=1>[F:10][C:8]1[CH:9]=[C:4]([CH:5]=[C:6]([C:19]2[CH:20]=[N:21][CH:22]=[CH:23][CH:24]=2)[CH:7]=1)[C:3]([OH:2])=[O:12]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 41980053-(1,3,2-Dioxaborinan-2-yl)pyridineHCID 21942598Methyl 3-bromo-5-fluorobenzoate

Product 1

HCID 21942438HCID 21942438, compoundYield 55.5%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
120 °C

Procedure

To the solution of Methyl-3-bromo-5-fluorobenzoate (1.97 g, 8.44 mmol) in toluene (40 ml) added Pyridine-3-boronic acid-1,3-propanediol ester (1.79 g, 7.63 mmol), potassium carbonate (11.66 g, 84.4 mmol) and tetrakis(triphenylphoshine)palladium (O) (0.49, 0.42 mmol), sequentially. The resulting brownish yellow reaction mixture was heated at 120° C. under argon overnight. The reaction mixture was cooled to room temperature, filtered through a pad of celite and concentrated in-vacuo. The residue was purified on silica gel using 1% methanol in dichloromethane to isolate the title compound (0.92 g, 47%) as a yellow solid.

Workup

  1. temperatureThe reaction mixture was cooled to room temperature
  2. filtrationfiltered through a pad of celite and
  3. concentrationconcentrated in-vacuo
  4. customThe residue was purified on silica gel using 1% methanol in dichloromethane

Sources & evidence

ORD record
ord-614059679a72406b95fdbce7ebc9c3fd
Source dataset
uspto-grants-2006_09
Patent number
US07112595B2

Reaction notes

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