Tricyclohexylphosphine → (5-(1,1,1-Trifluoro-2-hydroxypropan-2-yl)pyridin-3-yl)boronic acid

HRID 1521590Notes

Reaction equation

HRID 1521590 reaction equation
Br[C:2]1[CH:3]=[C:4]([C:8]([OH:14])([CH3:13])[C:9]([F:12])([F:11])[F:10])[CH:5]=[N:6][CH:7]=1.[B:15]1(B2OC(C)(C)C(C)(C)O2)[O:19]C(C)(C)C(C)(C)[O:16]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]>[F:10][C:9]([F:12])([F:11])[C:8]([C:4]1[CH:3]=[C:2]([B:15]([OH:19])[OH:16])[CH:7]=[N:6][CH:5]=1)([OH:14])[CH3:13]

Participants

7

Reactant 4

HCID 75806TricyclohexylphosphineHCID 517044Potassium AcetateHCID 2733548Bis(pinacolato)diboraneHCID 666852642-(5-Bromopyridin-3-yl)-1,1,1-trifluoropropan-2-ol

Product 1

HCID 89471688(5-(1,1,1-Trifluoro-2-hydroxypropan-2-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 55 Step A [enantiomer B (0.647 g, 2.40 mmol)], bis(pinacolato)diboron (1.22 g, 4.79 mmol), tris(dibenzylideneacetone)dipalladium (0) (0.439 g, 0.479 mmol), tricyclohexylphosphine (0.269 g, 0.958 mmol) and potassium acetate (0.705 g, 7.19 mmol) in 1,4-dioxane (12 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 235.95 [M+H]+.

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-2ba24341da9e4a8b952dd919eb5909c1
Source dataset
uspto-grants-2015_07
Patent number
US09073929B2

Reaction notes

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