Potassium Carbonate → HCID 86718614, compound

HRID 1480648Notes

Reaction equation

HRID 1480648 reaction equation
[Br:1][C:2]1[C:7]([OH:8])=[CH:6][CH:5]=[C:4](I)[N:3]=1.[Cl:10][C:11]1[CH:16]=[CH:15][C:14](B(O)O)=[CH:13][CH:12]=1.C(=O)([O-])[O-].[K+].[K+]>C(COC)OC.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>[Br:1][C:2]1[C:7]([OH:8])=[CH:6][CH:5]=[C:4]([C:14]2[CH:15]=[CH:16][C:11]([Cl:10])=[CH:12][CH:13]=2)[N:3]=1

Participants

7

Reactant 3

HCID 11430Potassium CarbonateHCID 742994-Chlorophenylboronic acidHCID 109794792-Bromo-6-iodopyridin-3-ol

Product 1

HCID 86718614HCID 86718614, compoundYield 52%

Reagents, catalysts & solvents 3

HCID 178418397HCID 178418397, compoundCatalystHCID 962WaterSolventHCID 80711,2-DimethoxyethaneSolvent

Conditions

Temperature
80 °C

Procedure

A mixture of 2-bromo-6-iodopyridin-3-ol (0.65 g, 2.167 mmol), 4-chlorobenzeneboronic acid (339 mg, 2.167 mmol) and potassium carbonate (749 mg, 5.419 mmol) in dimethoxyethane (15 mL) and water (5 mL) was purged with nitrogen for 20 minutes. Tetrakis(triphenylphosphine)palladium(0) (125.2 mg, 0.108 mmol) was added and the reaction mixture heated to 80° C. in a sealed vial for 15 hours. The cooled reaction mixture was partitioned between ethyl acetate (50 mL) and saturated aqueous ammonium chloride solution (50 mL), the organic phase separated, washed with water (50 mL) and saturated brine (50 mL), dried (MgSO4), filtered and concentrated under reduced pressure to give a yellow syrup. The crude product was purified by chromatography on silica eluting with a solvent gradient of 0 to 40% ethyl acetate in hexanes to give 2-bromo-6-(4-chlorophenyl)pyridin-3-ol (0.319 g, 52% yield) as a yellow crystalline solid.

Workup

  1. customwas purged with nitrogen for 20 minutes
  2. customThe cooled reaction mixture
  3. customwas partitioned between ethyl acetate (50 mL) and saturated aqueous ammonium chloride solution (50 mL)
  4. customthe organic phase separated
  5. washwashed with water (50 mL) and saturated brine (50 mL)
  6. dry with materialdried (MgSO4)
  7. filtrationfiltered
  8. concentrationconcentrated under reduced pressure
  9. customto give a yellow syrup
  10. customThe crude product was purified by chromatography on silica eluting with a solvent gradient of 0 to 40% ethyl acetate in hexanes

Sources & evidence

ORD record
ord-abbd2c082d0e445887fe8f3dad39ac42
Source dataset
uspto-grants-2016_08
Patent number
US09409893B2

Reaction notes

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