Potassium Acetate → {3-[(4-methoxybenzyl)oxy]-4-oxo-4H-1,2'-bipyridin-4'-yl}boronic acid

HRID 1056890Notes

Reaction equation

I[C:2]1[CH:7]=[CH:6][N:5]=[C:4]([N:8]2[CH:13]=[CH:12][C:11](=[O:14])[C:10]([O:15][CH2:16][C:17]3[CH:22]=[CH:21][C:20]([O:23][CH3:24])=[CH:19][CH:18]=3)=[CH:9]2)[CH:3]=1.[B:25]1(B2OC(C)(C)C(C)(C)O2)[O:29]C(C)(C)C(C)(C)[O:26]1.CC([O-])=O.[K+]>O1CCOCC1.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.Cl[Pd]Cl.[Fe+2]>[CH3:24][O:23][C:20]1[CH:21]=[CH:22][C:17]([CH2:16][O:15][C:10]2[C:11](=[O:14])[CH:12]=[CH:13][N:8]([C:4]3[CH:3]=[C:2]([B:25]([OH:29])[OH:26])[CH:7]=[CH:6][N:5]=3)[CH:9]=2)=[CH:18][CH:19]=1

Participants

Conditions

Temperature: 100 °C

Procedure

A mixture of 4′-iodo-3-[(4-methoxybenzyl)oxy]-4H-1,2′-bipyridin-4-one (5.6 g, 12.9 mmol), bis(pinacolato)diboron (4.91 g, 19.3 mmol), KOAc (2.53 g, 25.8 mmol), and Pd(dppf)Cl2 (0.6 g) in 1,4-dioxane (100 mL) was heated to 100° C. overnight. After cooling to room temperature, the reaction mixture was concentrated to give a residue which was purified by Prep-HPLC to give {3-[(4-methoxybenzyl)oxy]-4-oxo-4H-1,2′-bipyridin-4′-yl}boronic acid. !H NMR (DMSO, 400 MHz) S 8.61 (s, IH), 8.51 (d, J=4.4 Hz, IH), 8.437 (dd, J=8.0, 2.0 Hz, IH), 8.21 (d, J=2.4 Hz, IH), 8.00 (s, IH), 7.65 (d, J=4.8 Hz, IH), 7.36 (d, J=8.4 Hz, 2H), 6.92 (d, J=8.4 Hz, 2H)5 6.34 (d, J=7.6 Hz, H), 4.98 (s, 2H), 3.72 (s, 3H). MS (M+H)+ 353.2.

Workup

temperatureAfter cooling to room temperature
concentrationthe reaction mixture was concentrated
customto give a residue which
customwas purified by Prep-HPLC

Sources & evidence

ORD record: ord-1eecc47f1a39457a8e8ca5807502fc31
Source dataset: uspto-grants-2016_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09399651B2

Reaction notes

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