Potassium Acetate → HCID 90102148, compound

HRID 1052633Notes

Reaction equation

HRID 1052633 reaction equation
Br[C:2]1[CH:7]=[CH:6][N:5]=[C:4]([N:8]2[CH2:13][CH2:12][CH:11]([N:14]([CH3:16])[CH3:15])[CH2:10][CH2:9]2)[CH:3]=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>[CH3:15][N:14]([CH3:16])[CH:11]1[CH2:12][CH2:13][N:8]([C:4]2[CH:3]=[C:2]([B:17]([OH:21])[OH:18])[CH:7]=[CH:6][N:5]=2)[CH2:9][CH2:10]1

Participants

5

Reactant 3

HCID 517044Potassium AcetateHCID 2733548Bis(pinacolato)diboraneHCID 86810773HCID 86810773, compound

Product 1

HCID 90102148HCID 90102148, compoundYield 125.9%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

In a Schlenck vessel 1-(4-bromopyridin-2-yl)-N,N-dimethylpiperidin-4-amine (1.55 g, 5.45 mmol) was treated with bis(pinacolato)diboron (1.65 g, 6.50 mmol), potassium acetate (1.6 g, 16.3 mmol), bis(diphenylphosphino)ferrocene-palladium(II)dichloride dichloromethane complex (0.22 mg, 0.24 mmol) and dioxane (20 ml) as a solvent according to the method described in Preparation 174a to give 1.71 g (85% yield) of the title compound that was used in the next synthetic step without further purification. Purity 90%.

Sources & evidence

ORD record
ord-daabef35456b40f8a8a1d5ef0f1b943f
Source dataset
uspto-grants-2016_07
Patent number
US09388189B2

Reaction notes

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