Potassium Acetate → HCID 90102881, compound

HRID 1052570Notes

Reaction equation

HRID 1052570 reaction equation
Br[C:2]1[CH:3]=[C:4]([NH:8][C:9](=[O:18])[C:10]2[CH:15]=[CH:14][C:13]([O:16][CH3:17])=[CH:12][CH:11]=2)[CH:5]=[N:6][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+]>O1CCOCC1.C(OCC)(=O)C.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]>[CH3:17][O:16][C:13]1[CH:14]=[CH:15][C:10]([C:9]([NH:8][C:4]2[CH:3]=[C:2]([B:22]([OH:23])[OH:21])[CH:7]=[N:6][CH:5]=2)=[O:18])=[CH:11][CH:12]=1

Participants

7

Reactant 3

HCID 517044Potassium AcetateHCID 2733548Bis(pinacolato)diboraneHCID 90102824HCID 90102824, compound

Product 1

HCID 90102881HCID 90102881, compoundYield 110.4%

Reagents, catalysts & solvents 3

HCID 635956Ferrocene-1,1'-bis-(diphenylphosphine)CatalystHCID 8857Ethyl AcetateSolventHCID 312751,4-DioxaneSolvent

Conditions

Temperature
90 °C

Procedure

N-(5-Bromopyridin-3-yl)-4-methoxybenzamide (2.18 g, 7.06 mmol), 4,4,4′,4′,5,5,5′,5′-octamethyl-2,2′-bi(1,3,2-dioxaborolane) (5.6 g, 22 mmol), potassium acetate (2.7 g, 27.55 mmol), bis(diphenylphosphino)ferrocene-palladium(II)dichloride dichloromethane complex (680 mg, 0.83 mmol) and 1,1′-bis(diphenylphosphino)ferrocene (460 mg, 0.83 mmol) were suspended in dioxane (50 ml) and stirred at 90° C. overnight. The mixture was diluted with ethyl acetate and washed with water and brine, dried over sodium sulphate, filtered and evaporated under reduced pressure to give 2.12 g (100% yield) of the title compound. Purity (UPLC 92%, estimated 71%).

Workup

  1. washwashed with water and brine
  2. dry with materialdried over sodium sulphate
  3. filtrationfiltered
  4. customevaporated under reduced pressure

Sources & evidence

ORD record
ord-747e930e8eae471ba17a4fdd92b773c4
Source dataset
uspto-grants-2016_07
Patent number
US09388189B2

Reaction notes

Loading…