Potassium Carbonate → HCID 86700048, compound

HRID 1428098Notes

Reaction equation

HRID 1428098 reaction equation
[Br:1][C:2]1[C:3]([NH2:9])=[N:4][CH:5]=[C:6](I)[CH:7]=1.[CH3:10][O:11][C:12]1[CH:13]=[C:14](B(O)O)[CH:15]=[CH:16][C:17]=1[O:18][CH3:19].C(=O)([O-])[O-].[K+].[K+].[Cl-].[NH4+]>O1CCOCC1.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:3]([NH2:9])=[N:4][CH:5]=[C:6]([C:15]2[CH:14]=[CH:13][C:12]([O:11][CH3:10])=[C:17]([O:18][CH3:19])[CH:16]=2)[CH:7]=1

Participants

8

Reactant 4

HCID 11430Potassium CarbonateHCID 25517Ammonium ChlorideHCID 27347023,4-Dimethoxyphenylboronic acidHCID 176094413-Bromo-5-iodopyridin-2-amine

Product 1

HCID 86700048HCID 86700048, compoundYield 94.9%

Reagents, catalysts & solvents 3

HCID 178418397HCID 178418397, compoundCatalystHCID 962WaterSolventHCID 312751,4-DioxaneSolvent

Procedure

3-Bromo-5-iodopyridin-2-amine (7.50 g), 3,4-dimethoxyphenylboronic acid (4.79 g), tetrakis(triphenylphosphine)palladium (1.45 g) and potassium carbonate (10.4 g) were suspended in dioxane (100 ml) and water (10 ml), and the suspension was heated at 80° C. for 9.5 hours. After leaving to cool, a saturated aqueous ammonium chloride solution was added, and the organic layer was extracted with ethyl acetate and dried over sodium sulfate. The solvent was distilled off under reduced pressure, and the residue was purified by silica gel column chromatography [ethyl acetate] to give 7.36 g of the title compound as a solid.

Workup

  1. customAfter leaving
  2. temperatureto cool
  3. extractionthe organic layer was extracted with ethyl acetate
  4. dry with materialdried over sodium sulfate
  5. distillationThe solvent was distilled off under reduced pressure
  6. customthe residue was purified by silica gel column chromatography [ethyl acetate]

Sources & evidence

ORD record
ord-a53daad04b8b4a6090092417a66ae3e6
Source dataset
uspto-grants-2015_01
Patent number
US08933103B2

Reaction notes

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