Potassium Acetate → HCID 90102593, compound

HRID 1052578Notes

Reaction equation

HRID 1052578 reaction equation
Br[C:2]1[CH:3]=[C:4]([NH:8][C:9](=[O:18])[C:10]2[CH:15]=[CH:14][CH:13]=[C:12]([O:16][CH3:17])[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:12]1[CH:11]=[C:10]([CH:15]=[CH:14][CH:13]=1)[C:9]([NH:8][C:4]1[CH:3]=[C:2]([B:22]([OH:23])[OH:21])[CH:7]=[N:6][CH:5]=1)=[O:18]

Participants

7

Reactant 3

HCID 517044Potassium AcetateHCID 2733548Bis(pinacolato)diboraneHCID 90102438HCID 90102438, compound

Product 1

HCID 90102593HCID 90102593, compoundYield 47.7%

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)-3-methoxybenzamide (3.07 g, 7.71 mmol), 4,4,4′,4′,5,5,5′,5′-octamethyl-2,2′-bi(1,3,2-dioxaborolane) (5.88 g, 23.16 mmol), potassium acetate (3.79 g, 38.62 mmol), bis(diphenylphosphino)ferrocene-palladium(II)dichloride dichloromethane complex (950 mg, 1.16 mmol) and 1,1′-bis(diphenylphosphino)ferrocene (640 mg, 1.16 mmol) were suspended in dioxane (60 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. The crude was purified by reverse phase using SP1® Purification System to give 1 g (44% yield) of the title compound. Purity 93%.

Workup

  1. washwashed with water and brine
  2. dry with materialdried over sodium sulphate
  3. filtrationfiltered
  4. customevaporated under reduced pressure
  5. customThe crude was purified by reverse phase
  6. custom® Purification System

Sources & evidence

ORD record
ord-83f1ce9bcc064a8f9abb333b1c685612
Source dataset
uspto-grants-2016_07
Patent number
US09388189B2

Reaction notes

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