Boronic Acid → (6-((2-Methoxyacetamido)methyl)pyridin-3-yl)boronic acid

HRID 877786Notes

Reaction equation

HRID 877786 reaction equation
Br[C:2]1[CH:3]=[CH:4][C:5]([CH2:8][NH:9][C:10](=[O:14])[CH2:11][O:12][CH3:13])=[N:6][CH:7]=1.CC1(C)C(C)(C)[O:19][B:18](B2OC(C)(C)C(C)(C)O2)[O:17]1.C([O-])(=O)C.[K+].B(O)O>O1CCOCC1>[CH3:13][O:12][CH2:11][C:10]([NH:9][CH2:8][C:5]1[N:6]=[CH:7][C:2]([B:18]([OH:19])[OH:17])=[CH:3][CH:4]=1)=[O:14]

Participants

6

Reactant 4

HCID 61668Boronic AcidHCID 517044Potassium AcetateHCID 2733548Bis(pinacolato)diboraneHCID 68291149N-((5-bromopyridin-2-yl)methyl)-2-methoxyacetamide

Product 1

HCID 68291194(6-((2-Methoxyacetamido)methyl)pyridin-3-yl)boronic acidYield 100.1%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

A mixture N-((5-bromopyridin-2-yl)methyl)-2-methoxyacetamide (387 mg, 1.494 mmol), 4,4,4′,4′,5,5,5′,5′-octamethyl-2,2′-bi(1,3,2-dioxaborolane) (493 mg, 1.942 mmol), PdCl2(dppf)-CH2Cl2Adduct (122 mg, 0.149 mmol) and potassium acetate (366 mg, 3.73 mmol) in dioxane (10 mL) was heated to 70° C. for 3 hr. LCMS indicated that the major product was boronic acid. After cooling to rt, the reaction mixture was filtered through celite and the filtrate was concentrated to afford (6-((2-methoxyacetamido)methyl)-pyridin-3-yl)boronic acid (335 mg, 1.495 mmol, 100% yield) as a brown oil. The material was used as is in the next step. MS (ES+) m/z: 225.0 (M+H); LC retention time: 0.38 min (analytical LCMS Method B).

Workup

  1. filtrationthe reaction mixture was filtered through celite
  2. concentrationthe filtrate was concentrated

Sources & evidence

ORD record
ord-331ae19acdab49a8bc1bd2e641fb84cb
Source dataset
uspto-grants-2015_03
Patent number
US08987268B2

Reaction notes

Loading…