Potassium Acetate → (6-Cyano-4'-(ethylsulfonyl)-2'-methoxy-[1,1'-biphenyl]-3-yl)boronic acid

HRID 1846041Notes

Reaction equation

HRID 1846041 reaction equation
Cl[C:2]1[CH:7]=[C:6]([C:8]2[CH:13]=[CH:12][C:11]([S:14]([CH2:17][CH3:18])(=[O:16])=[O:15])=[CH:10][C:9]=2[O:19][CH3:20])[C:5]([C:21]#[N:22])=[CH:4][CH:3]=1.C([O-])(=O)C.[K+].[B:28]1(B2OC(C)(C)C(C)(C)O2)[O:32]C(C)(C)C(C)(C)[O:29]1>O1CCOCC1.C1(P([C-]2C=CC=C2)C2C=CC=CC=2)C=CC=CC=1.[C-]1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=C1.[Fe+2].[Pd](Cl)Cl>[C:21]([C:5]1[C:6]([C:8]2[CH:13]=[CH:12][C:11]([S:14]([CH2:17][CH3:18])(=[O:16])=[O:15])=[CH:10][C:9]=2[O:19][CH3:20])=[CH:7][C:2]([B:28]([OH:32])[OH:29])=[CH:3][CH:4]=1)#[N:22]

Participants

6

Reactant 3

HCID 517044Potassium AcetateHCID 2733548Bis(pinacolato)diboraneHCID 867232635-Chloro-4'-(ethylsulfonyl)-2'-methoxy-[1,1'-biphenyl]-2-carbonitrile

Product 1

HCID 86723224(6-Cyano-4'-(ethylsulfonyl)-2'-methoxy-[1,1'-biphenyl]-3-yl)boronic acidYield 25%

Reagents, catalysts & solvents 2

HCID 178418228Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)CatalystHCID 312751,4-DioxaneSolvent

Procedure

To a solution of 5-chloro-4′-(ethylsulfonyl)-2′-methoxy-[1,1′-biphenyl]-2-carbonitrile (Preparation 66, 330 mg, 0.985 mmol) in dioxane (5 mL) was added bis(diphenylphosphino)ferrocene-palladium(II)dichloride (30 mg, 0.12 mmol), potassium acetate (290 mg, 2.95 mmol) and bis(pinacolato)diboron (3.75 mg, 1.48 mmol). The reaction was degassed and then placed on a preheated hot plate (100° C.) for 16 hours. The reaction mixture was cooled to room temperature, filtered through celite and the solvent removed in vacuo. The crude material was purified by reverse phase column chromatography eluting with MeCN/H2O to hydrolyse the boronic ester to afford the title compound in 25% yield, 85 mg.

Workup

  1. customThe reaction was degassed
  2. filtrationfiltered through celite
  3. customthe solvent removed in vacuo
  4. customThe crude material was purified by reverse phase column chromatography
  5. washeluting with MeCN/H2O

Sources & evidence

ORD record
ord-0201dd47b48044c99a2f69628ea63781
Source dataset
uspto-grants-2015_02
Patent number
US08952008B2

Reaction notes

Loading…