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

HRID 1521599Notes

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]

Participants

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

customwas flushed with nitrogen
customsealed tightly
temperatureThe reaction was then cooled to room temperature
custompassed through a syringe
filtrationfilter
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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