Tricyclohexylphosphine → [5-(Oxetan-3-yl)pyridin-3-yl]boronic acid

HRID 1521598Notes

Reaction equation

HRID 1521598 reaction equation
Br[C:2]1[CH:3]=[N:4][CH:5]=[C:6]([CH:8]2[CH2:11][O:10][CH2:9]2)[CH:7]=1.[B:12]1(B2OC(C)(C)C(C)(C)O2)[O:16]C(C)(C)C(C)(C)[O:13]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]>[O:10]1[CH2:11][CH:8]([C:6]2[CH:7]=[C:2]([B:12]([OH:16])[OH:13])[CH:3]=[N:4][CH:5]=2)[CH2:9]1

Participants

7

Reactant 4

HCID 75806TricyclohexylphosphineHCID 517044Potassium AcetateHCID 2733548Bis(pinacolato)diboraneHCID 726987543-Bromo-5-(oxetan-3-YL)pyridine

Product 1

HCID 89961635[5-(Oxetan-3-yl)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 63 Step A (45 mg, 0.21 mmol), bis(pinacolato)diboron (107 mg, 0.420 mmol), tris(dibenzylideneacetone)dipalladium (0) (38.5 mg, 0.042 mmol), tricyclohexylphosphine (23.6 mg, 0.084 mmol) and potassium acetate (61.9 mg, 0.631 mmol) in dioxane (1.0 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 which was used without further purification.

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-bfb3c49e7d86446fbc4a28cdd1e56d9a
Source dataset
uspto-grants-2015_07
Patent number
US09073929B2

Reaction notes

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