Tricyclohexylphosphine → (5-(2-(Ethylsulfonyl)propan-2-yl)pyridin-3-yl)boronic acid

HRID 1521595Notes

Reaction equation

Br[C:2]1[CH:3]=[N:4][CH:5]=[C:6]([C:8]([S:11]([CH2:14][CH3:15])(=[O:13])=[O:12])([CH3:10])[CH3:9])[CH:7]=1.[B:16]1(B2OC(C)(C)C(C)(C)O2)[O:20]C(C)(C)C(C)(C)[O:17]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]>[CH2:14]([S:11]([C:8]([C:6]1[CH:7]=[C:2]([B:16]([OH:20])[OH:17])[CH:3]=[N:4][CH:5]=1)([CH3:10])[CH3:9])(=[O:13])=[O:12])[CH3:15]

Participants

Conditions

Temperature: 80 °C

Procedure

A vial containing the title compound from Example 62 Step D (0.030 g, 0.103 mmol), bis(pinacolato)diboron (0.052 g, 0.205 mmol), tris(dibenzylideneacetone)dipalladium (0) (0.019 g, 0.021 mmol), tricyclohexylphosphine (0.012 g, 0.041 mmol) and potassium acetate (0.030 g, 0.308 mmol) in 1,4-dioxane (0.510 mL) was flushed with nitrogen, sealed tightly and heated to 80° C. overnight. The reaction was then passed through a syringe filter and concentrated under reduced pressure to provide the title compound: LCMS m/z 258.29 [M+H]+.

Workup

customwas flushed with nitrogen
customsealed tightly
customThe reaction was then passed through a syringe
filtrationfilter
concentrationconcentrated under reduced pressure

Sources & evidence

ORD record: ord-12c3bc0fed8f4c32b6983904c6dc1d62
Source dataset: uspto-grants-2015_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09073929B2

Reaction notes

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