Potassium Acetate → 5-(3-Cyclopropyl-1H-pyrazol-5-ylamino)-1-methyl-6-oxo-1,6-dihydropyridin-3-ylboronic Acid

HRID 407694Notes

Reaction equation

Br[C:2]1[CH:3]=[C:4]([NH:10][C:11]2[NH:15][N:14]=[C:13]([CH:16]3[CH2:18][CH2:17]3)[CH:12]=2)[C:5](=[O:9])[N:6]([CH3:8])[CH:7]=1.CC1(C)C(C)(C)[O:23][B:22](B2OC(C)(C)C(C)(C)O2)[O:21]1.C([O-])(=O)C.[K+]>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].O1CCOCC1>[CH:16]1([C:13]2[CH:12]=[C:11]([NH:10][C:4]3[C:5](=[O:9])[N:6]([CH3:8])[CH:7]=[C:2]([B:22]([OH:23])[OH:21])[CH:3]=3)[NH:15][N:14]=2)[CH2:18][CH2:17]1

Participants

Conditions

Temperature: 105 °C

Procedure

A 50-mL single-neck round-bottomed flask equipped with a magnetic stirrer and a reflux condenser was charged with 126d (205 mg, 0.665 mmol), 4,4,4′,4′,5,5,5′,5′-octamethyl-2,2′-bi(1,3,2-dioxaborolane) (1.0 g, 4.0 mmol), dioxane (16 mL), PdCl2(dppf) (54.3 mg, 0.066 mmol), and potassium acetate (0.39 mg, 4.0 mmol). After bubbling argon through the resulting mixture for 30 minutes, it was stirred at 105° C. for 4 h under argon atmosphere. It was then cooled to room temperature and filtered. The filtrate was evaporated under reduced pressure to afford crude 126e, which was used without further purification. MS: [M+H]+ 275.

Workup

customA 50-mL single-neck round-bottomed flask equipped with a magnetic stirrer and a reflux condenser
customAfter bubbling argon through the resulting mixture for 30 minutes
temperatureIt was then cooled to room temperature
filtrationfiltered
customThe filtrate was evaporated under reduced pressure

Sources & evidence

ORD record: ord-f656774c4c7441d59a451b332fa751c5
Source dataset: uspto-grants-2014_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08754077B2

Reaction notes

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