Tricyclohexylphosphine → HCID 70977491, compound

HRID 1521605Notes

Reaction equation

HRID 1521605 reaction equation
Br[C:2]1[CH:3]=[C:4]([C:8]2([C:11]([O:13][CH3:14])=[O:12])[CH2:10][CH2:9]2)[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+]>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>[CH3:14][O:13][C:11]([C:8]1([C:4]2[CH:3]=[C:2]([B:15]([OH:19])[OH:16])[CH:7]=[N:6][CH:5]=2)[CH2:10][CH2:9]1)=[O:12]

Participants

7

Reactant 4

HCID 75806TricyclohexylphosphineHCID 517044Potassium AcetateHCID 2733548Bis(pinacolato)diboraneHCID 59578399Methyl 1-(5-bromopyridin-3-yl)cyclopropanecarboxylate

Product 1

HCID 70977491HCID 70977491, compound

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 71 Step B (0.150 g, 0.586 mmol), bis(pinacolato)diboron (0.178 g, 0.703 mmol), tris(dibenzylideneacetone)dipalladium (0) (0.054 g, 0.059 mmol), tricyclohexylphosphine (0.033 g, 0.117 mmol) and potassium acetate (0.17 g, 1.76 mmol) was added dioxane (5.9 mL). The reaction was heated to 80° C. for 16 hours. It was then cooled to room temperature, passed through a syringe filter and concentrated under reduced pressure to afford the title compound: LCMS m/z 221.63 [M+H]+.

Workup

  1. temperatureIt was then cooled to room temperature
  2. custompassed through a syringe
  3. filtrationfilter
  4. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-fa6fbae1abb14217b18e3565efe9b0a9
Source dataset
uspto-grants-2015_07
Patent number
US09073929B2

Reaction notes

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