Tricyclohexylphosphine → (5-(2-Methoxypropan-2-yl)pyridin-3-yl)boronic acid
Reaction equation
Br[C:2]1[CH:3]=[N:4][CH:5]=[C:6]([C:8]([O:11][CH3:12])([CH3:10])[CH3:9])[CH:7]=1.[B:13]1(B2OC(C)(C)C(C)(C)O2)[O:17]C(C)(C)C(C)(C)[O:14]1.C([O-])(=O)C.[K+].C1(P(C2CCCCC2)C2CCCCC2)CCCCC1>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].O1CCOCC1>[CH3:12][O:11][C:8]([C:6]1[CH:7]=[C:2]([B:13]([OH:17])[OH:14])[CH:3]=[N:4][CH:5]=1)([CH3:10])[CH3:9]Participants
7
Reactant 4
Product 1
Reagents, catalysts & solvents 2
Conditions
- Temperature
- 80 °C
Procedure
To a vial containing the title compound from Example 49 Step A (0.07 g, 0.30 mmol), bis(pinacolato)diboron (0.093 g, 0.37 mmol), potassium acetate (0.090 g, 0.91 mmol), tris(dibenzylideneacetone)dipalladium (0) (0.028 g, 0.030 mmol) and tricyclohexylphosphine (0.017 g, 0.061 mmol) was added 1,4-dioxane (3.0 mL). The vial was flushed with nitrogen, sealed tightly and heated to 80° C. overnight. The reaction was then concentrated under reduced pressure to provide the title compound which was used without further purification.
Workup
- customThe vial was flushed with nitrogen
- customsealed tightly
- concentrationThe reaction was then concentrated under reduced pressure
Sources & evidence
- ORD record
- ord-53d577ebc0b048af98fed108d0035ac2
- Source dataset
- uspto-grants-2015_07
- Patent number
- US09073929B2
Reaction notes
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