Potassium Acetate → (3-(Methylsulfonamido)-5-(trifluoromethyl)phenyl)boronic acid

HRID 1052574Notes

Reaction equation

Br[C:2]1[CH:3]=[C:4]([NH:12][S:13]([CH3:16])(=[O:15])=[O:14])[CH:5]=[C:6]([C:8]([F:11])([F:10])[F:9])[CH:7]=1.[B:17]1(B2OC(C)(C)C(C)(C)O2)[O:21]C(C)(C)C(C)(C)[O:18]1.C([O-])(=O)C.[K+]>O1CCOCC1.C1(P(C2C=CC=CC=2)[C-]2C=CC=C2)C=CC=CC=1.[C-]1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=C1.[Fe+2]>[CH3:16][S:13]([NH:12][C:4]1[CH:3]=[C:2]([B:17]([OH:21])[OH:18])[CH:7]=[C:6]([C:8]([F:11])([F:10])[F:9])[CH:5]=1)(=[O:15])=[O:14]

Participants

Conditions

Temperature: 90 °C

Procedure

N-(3-Bromo-5-(trifluoromethyl)phenyl)methanesulfonamide (1.33 g, 4.06 mmol), bis(pinacolato)diboron (4.12 g, 16.22 mmol), potassium acetate (2 g, 20.38 mmol), bis(diphenylphosphino)ferrocene-palladium(II)dichloride dichloromethane complex (500 mg, 0.61 mmol) and 1,1′-bis(diphenylphosphino)ferrocene (340 mg, 0.61 mmol) were suspended in dioxane (35 ml) and stirred at 90° C. for 48 h. After evaporation of the solvent under reduced pressure, ethyl acetate (100 ml) was added to the residue and the precipitated salts were eliminated by filtration. The solvent was evaporated under reduced pressure to give 6.39 g (100% yield) of the title compound as a mixture of (3-(methylsulfonamido)-5-(trifluoromethyl)phenyl)boronic acid and N-(3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-5-(trifluoromethyl)phenyl)methanesulfonamide that was used in next step without further purification. (1:1). Estimated Purity: 24%

Workup

customAfter evaporation of the solvent under reduced pressure, ethyl acetate (100 ml)
additionwas added to the residue
filtrationthe precipitated salts were eliminated by filtration
customThe solvent was evaporated under reduced pressure

Sources & evidence

ORD record: ord-0ace7734af214c509c557f2391a833b5
Source dataset: uspto-grants-2016_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09388189B2

Reaction notes

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