Potassium Phosphate, Tribasic → HCID 22317976, compound

HRID 1446091Notes

Reaction equation

HRID 1446091 reaction equation
I[C:2]1[CH:7]=[CH:6][C:5]([Br:8])=[CH:4][N:3]=1.[C:9](B1OC(C)(C)C(C)(C)O1)([CH3:11])=[CH2:10].P([O-])([O-])([O-])=O.[K+].[K+].[K+]>COCCOC.O.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:5]1[CH:6]=[CH:7][C:2]([C:9]([CH3:11])=[CH2:10])=[N:3][CH:4]=1

Participants

7

Reactant 3

HCID 62657Potassium Phosphate, TribasicHCID 5936905-Bromo-2-iodopyridineHCID 109974264,4,5,5-Tetramethyl-2-(prop-1-en-2-yl)-1,3,2-dioxaborolane

Product 1

HCID 22317976HCID 22317976, compound

Reagents, catalysts & solvents 3

HCID 178418228Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)CatalystHCID 962WaterSolventHCID 80711,2-DimethoxyethaneSolvent

Conditions

Temperature
80 °C

Procedure

5-Bromo-2-isopropenyl-pyridine was prepared according to the scheme shown in FIG. 9. In the sealed round bottom flask, 2-Iodo-5-bromopyridine (4.34 g, 15.3 mmol), isopropenylboronic acid pinacol ester (2.57 g, 15.3 mmol), PdCl2(dppf) (1.87 g, 2.3 mmol) and potassium phosphate (8.2 g, 38 mmol) were dissolved in 25 mL DME and 8 mL water. The resulting solution was stirred at 80° C. for 3 hours and was then cooled down to room temperature. After separation, the aqueous phase was extracted with EtOAc. The combined organic layers were washed with brine and dried over Na2SO4. After removing the solvent, fairly pure product (about 3.0 g) was obtained as yellow solid, which was directly used for next step without further purification. ESI MS m/z 198, 200 (M+H).

Workup

  1. temperaturewas then cooled down to room temperature
  2. customAfter separation
  3. extractionthe aqueous phase was extracted with EtOAc
  4. washThe combined organic layers were washed with brine
  5. dry with materialdried over Na2SO4
  6. customAfter removing the solvent

Sources & evidence

ORD record
ord-d235dfdfce544adf8ff6620ebe5ec44e
Source dataset
uspto-grants-2010_02
Patent number
US07666864B2

Reaction notes

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