Tricyclohexylphosphine → (5-(1-Vinylcyclopropyl)pyridin-3-yl)boronic acid

HRID 1521615Notes

Reaction equation

HRID 1521615 reaction equation
Br[C:2]1[CH:3]=[N:4][CH:5]=[C:6]([C:8]2([CH:11]=[CH2:12])[CH2:10][CH2:9]2)[CH:7]=1.[B:13]1(B2OC(C)(C)C(C)(C)O2)[O:17]C(C)(C)C(C)(C)[O:14]1.C1(P(C2CCCCC2)C2CCCCC2)CCCCC1.C([O-])(=O)C.[K+]>O1CCOCC1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd]>[CH:11]([C:8]1([C:6]2[CH:7]=[C:2]([B:13]([OH:17])[OH:14])[CH:3]=[N:4][CH:5]=2)[CH2:10][CH2:9]1)=[CH2:12]

Participants

7

Reactant 4

HCID 75806TricyclohexylphosphineHCID 517044Potassium AcetateHCID 2733548Bis(pinacolato)diboraneHCID 891559033-Bromo-5-(1-ethenylcyclopropyl)pyridine

Product 1

HCID 89961615(5-(1-Vinylcyclopropyl)pyridin-3-yl)boronic acid

Reagents, catalysts & solvents 2

HCID 9811564Bis(dibenzylideneacetone)palladiumCatalystHCID 312751,4-DioxaneSolvent

Conditions

Temperature
80 °C

Procedure

A vial containing the title compound from Example 73 Step C (0.036 g, 0.161 mmol), bis(pinacolato)diboron (0.082 g, 0.321 mmol), tris(dibenzylideneacetone)-dipalladium (0) (0.029 g, 0.032 mmol), tricyclohexylphosphine (0.018 g, 0.064 mmol) and potassium acetate (0.047 g, 0.48 mmol) in dioxane (0.80 mL) was flushed with nitrogen, sealed tightly and heated to 80° C. overnight. The reaction was then passed through a syringe filter and concentrated under reduced pressure to provide the title compound: LCMS m/z 189.12 [M]+.

Workup

  1. customwas flushed with nitrogen
  2. customsealed tightly
  3. customThe reaction was then passed through a syringe
  4. filtrationfilter
  5. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-5031391e519c4ba2ab2871b5b953f2e1
Source dataset
uspto-grants-2015_07
Patent number
US09073929B2

Reaction notes

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