Potassium Acetate → {2-[(Oxan-4-yl)oxy]pyridin-4-yl}boronic acid

HRID 1894182Notes

Reaction equation

Br[C:2]1[CH:7]=[CH:6][N:5]=[C:4]([O:8][CH:9]2[CH2:14][CH2:13][O:12][CH2:11][CH2:10]2)[CH:3]=1.CC1(C)C(C)(C)[O:19][B:18](B2OC(C)(C)C(C)(C)O2)[O:17]1.C([O-])(=O)C.[K+]>CS(C)=O>[O:12]1[CH2:13][CH2:14][CH:9]([O:8][C:4]2[CH:3]=[C:2]([B:18]([OH:19])[OH:17])[CH:7]=[CH:6][N:5]=2)[CH2:10][CH2:11]1

Participants

Conditions

Temperature: 100 °C

Procedure

To 4-Bromo-2-(tetrahydro-pyran-4-yloxy)-pyridine (0.2 g, 0.77 mmol) in DMSO (5 ml) (degassed by bubbling N2 through) was added 4,4,5,5,4′,4′,5′,5′-Octamethyl-2,2′-bi-1,3,2-dioxaborolane (0.39 g, 1.55 mmol) and potassium acetate (0.27 g, 2.31 mmol). PdCl2ddpf (0.028, 0.04 mmol) was added, the reaction mixture again degassed and then heated at 100° C. for 5 h. The compound was passed through a C18 reverse phase chromatography column to afford the desired product, used crude. MS: [MH]+ 224.

Workup

additionPdCl2ddpf (0.028, 0.04 mmol) was added
customthe reaction mixture again degassed

Sources & evidence

ORD record: ord-c79f140241724c12bfd88b8e339b34d6
Source dataset: uspto-grants-2013_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08513276B2

Reaction notes

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