Tricyclohexylphosphine → [5-[1-(3-Cyclopropyl-1,2,4-oxadiazol-5-yl)cyclopropyl]-3-pyridinyl]boronic acid

HRID 1521610Notes

Reaction equation

HRID 1521610 reaction equation
Br[C:2]1[CH:3]=[N:4][CH:5]=[C:6]([C:8]2([C:11]3[O:15][N:14]=[C:13]([CH:16]4[CH2:18][CH2:17]4)[N:12]=3)[CH2:10][CH2:9]2)[CH:7]=1.[B:19]1(B2OC(C)(C)C(C)(C)O2)[O:23]C(C)(C)C(C)(C)[O:20]1.C1(P(C2CCCCC2)C2CCCCC2)CCCCC1.C([O-])(=O)C.[K+]>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>[CH:16]1([C:13]2[N:12]=[C:11]([C:8]3([C:6]4[CH:7]=[C:2]([B:19]([OH:23])[OH:20])[CH:3]=[N:4][CH:5]=4)[CH2:10][CH2:9]3)[O:15][N:14]=2)[CH2:18][CH2:17]1

Participants

7

Reactant 4

HCID 75806TricyclohexylphosphineHCID 517044Potassium AcetateHCID 2733548Bis(pinacolato)diboraneHCID 899617073-Bromo-5-[1-(3-cyclopropyl-1,2,4-oxadiazol-5-yl)cyclopropyl]pyridine

Product 1

HCID 89961641[5-[1-(3-Cyclopropyl-1,2,4-oxadiazol-5-yl)cyclopropyl]-3-pyridinyl]boronic acid

Reagents, catalysts & solvents 2

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

Conditions

Temperature
80 °C

Procedure

To a vial containing the title compound from Example 72 Step B (0.03 g, 0.10 mmol), bis(pinacolato)diboron (0.050 g, 0.20 mmol), tris(dibenzylideneacetone)dipalladium (0) (0.018 g, 0.020 mmol), tricyclohexylphosphine (11 mg, 0.039 mmol) and potassium acetate (0.029 g, 0.294 mmol) was added 1,4-dioxane (1.0 ml). The vial was capped tightly and heated to 80° C. overnight. The reaction was then concentrated under reduced pressure to provide the title compound: LCMS m/z 245.70 [M+H]+.

Workup

  1. customThe vial was capped tightly
  2. concentrationThe reaction was then concentrated under reduced pressure

Sources & evidence

ORD record
ord-65aabc83fbb44bce896ead2c4425b322
Source dataset
uspto-grants-2015_07
Patent number
US09073929B2

Reaction notes

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