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Tricyclohexylphosphine → 5-(2-Methyl-1-(trifluoromethoxy)propan-2-yl)pyridin-3-ylboronic acid

HRID 1521599
Notes
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Reaction equation

HRID 1521599 reaction equation
Br[C:2]1[CH:3]=[N:4][CH:5]=[C:6]([C:8]([CH3:16])([CH3:15])[CH2:9][O:10][C:11]([F:14])([F:13])[F:12])[CH:7]=1.[B:17]1(B2OC(C)(C)C(C)(C)O2)[O:21]C(C)(C)C(C)(C)[O:18]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]>[CH3:15][C:8]([C:6]1[CH:7]=[C:2]([B:17]([OH:21])[OH:18])[CH:3]=[N:4][CH:5]=1)([CH3:16])[CH2:9][O:10][C:11]([F:14])([F:13])[F:12]
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

7

Reactant 4

HCID 75806TricyclohexylphosphineHCID 517044Potassium AcetateHCID 2733548Bis(pinacolato)diboraneHCID 709788013-Bromo-5-(2-methyl-1-(trifluoromethoxy)propan-2-yl)pyridine

Product 1

HCID 709812375-(2-Methyl-1-(trifluoromethoxy)propan-2-yl)pyridin-3-ylboronic acid

Reagents, catalysts & solvents 2

HCID 9811564
Bis(dibenzylideneacetone)palladium
Catalyst
HCID 312751,4-DioxaneSolvent

Conditions

Temperature
80 °C

Procedure

A vial containing the title compound from Example 64 Step B (80 mg, 0.27 mmol), bis(pinacolato)diboron (136 mg, 0.537 mmol), tris(dibenzylideneacetone)dipalladium (0) (49.1 mg, 0.054 mmol), tricyclohexylphosphine (30.1 mg, 0.107 mmol) and potassium acetate (79 mg, 0.805 mmol) in 1,4-dioxane (1.3 mL) was flushed with nitrogen, sealed tightly and heated to 80° C. overnight. The reaction was then cooled to room temperature and passed through a syringe filter. The resulting solution was then concentrated under reduced pressure to afford the title compound which was used without further purification.

Workup

  1. customwas flushed with nitrogen
  2. customsealed tightly
  3. temperatureThe reaction was then cooled to room temperature
  4. custompassed through a syringe
  5. filtrationfilter
  6. concentrationThe resulting solution was then concentrated under reduced pressure

Sources & evidence

ORD record
ord-2ece2ab65bfc4e96a9a6be45c3c19162
Source dataset
uspto-grants-2015_07
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US09073929B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes