Potassium Carbonate → HCID 90412467, compound

HRID 1521937Notes

Reaction equation

HRID 1521937 reaction equation
[Br:1][C:2]1[C:7]([Cl:8])=[CH:6][CH:5]=[C:4](I)[N:3]=1.[C:10]1(B(O)O)[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1.C(=O)([O-])[O-].[K+].[K+]>C(#N)C>[Br:1][C:2]1[C:7]([Cl:8])=[CH:6][CH:5]=[C:4]([C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)[N:3]=1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 66827Phenylboronic AcidHCID 90414154HCID 90414154, compound

Product 1

HCID 90412467HCID 90412467, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Conditions

Temperature
70 °C

Procedure

To a degassed solution of 2-bromo-3-chloro-6-iodopyridine (350 mg, 1.099 mmol) and phenylboronic acid (134 mg, 1.099 mmol), saturated potassium carbonate solution (5.50 mL, 5.50 mmol) in acetonitrile (5 mL) was added tetrakistriphenylphosphine palladium (63.5 mg, 0.055 mmol) and the mixture heated at 70° C. for 2 hours. The mixture was cooled and filtered through diatomaceous earth. The filtrate was concentrated and the residue washed with diethyl ether to afford the crude title compound. LCMS: 267 (M+H)+.

Workup

  1. temperatureThe mixture was cooled
  2. filtrationfiltered through diatomaceous earth
  3. concentrationThe filtrate was concentrated
  4. washthe residue washed with diethyl ether

Sources & evidence

ORD record
ord-75792dce06e345f29ab451bf1cd31399
Source dataset
uspto-grants-2015_07
Patent number
US09073922B2

Reaction notes

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