Potassium Carbonate → HCID 59526200, compound

HRID 385813Notes

Reaction equation

HRID 385813 reaction equation
Br[C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([Br:8])[N:3]=1.C(=O)([O-])[O-].[K+].[K+].CC1(C)C(C)(C)OB([C:23]2[CH2:24][CH2:25][O:26][CH2:27][CH:28]=2)O1>CN(C=O)C.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.Cl[Pd]Cl.[Fe+2]>[Br:8][C:4]1[CH:5]=[CH:6][CH:7]=[C:2]([C:23]2[CH2:28][CH2:27][O:26][CH2:25][CH:24]=2)[N:3]=1

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 122742,6-DibromopyridineHCID 112180533,6-Dihydro-2H-pyran-4-boronic acid pinacol ester

Product 1

HCID 59526200HCID 59526200, compound

Reagents, catalysts & solvents 2

HCID 178418228Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)CatalystHCID 6228DimethylformamideSolvent

Conditions

Temperature
80 °C

Procedure

2,6-Dibromopyridine (710 mg, 3.00 mmol), potassium carbonate (1184 mg, 8.57 mmol), PdCl2(dppf) (104 mg, 0.14 mmol) were placed in a flask and the flask was purged with argon. 4-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)-3,6-dihydro-2H-pyran (600 mg, 2.86 mmol) was dissolved in degassed DMF (19 mL), added to the reaction mixture and 5 argon/vacuum purge cycles were performed. The reaction was heated at 80° C. overnight. The reaction was cooled to room temperature, diluted with ethyl acetate, washed with water, dried over magnesium sulfate, filtered, and concentrated. The crude mixture was purified by silica gel chromatography to yield the title compound.

Workup

  1. customthe flask was purged with argon
  2. additionadded to the reaction mixture and 5 argon/vacuum
  3. custompurge cycles
  4. temperatureThe reaction was cooled to room temperature
  5. additiondiluted with ethyl acetate
  6. washwashed with water
  7. dry with materialdried over magnesium sulfate
  8. filtrationfiltered
  9. concentrationconcentrated
  10. customThe crude mixture was purified by silica gel chromatography

Sources & evidence

ORD record
ord-674585a2ded64f8b942a846770f6a4fc
Source dataset
uspto-grants-2013_02
Patent number
US08367706B2

Reaction notes

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