Potassium Acetate → 2,4-Difluoro-3-(pyridin-3-yl)benzeneboronic acid

HRID 2183932노트

반응식

HRID 2183932 반응식
Br[C:2]1[C:3]([F:15])=[C:4]([C:9]2[CH:10]=[N:11][CH:12]=[CH:13][CH:14]=2)[C:5]([F:8])=[CH:6][CH:7]=1.C([O-])(=O)C.[K+].[B:21]1(B2OCC(C)(C)CO2)[O:26]CC(C)(C)C[O:22]1>O1CCOCC1>[F:15][C:3]1[C:4]([C:9]2[CH:10]=[N:11][CH:12]=[CH:13][CH:14]=2)=[C:5]([F:8])[CH:6]=[CH:7][C:2]=1[B:21]([OH:26])[OH:22]

참가 물질

5

반응물 3

HCID 517044Potassium AcetateHCID 2734316Bis(neopentyl glycolato)diboronHCID 222400863-(3-Bromo-2,6-difluorophenyl)pyridine

생성물 1

HCID 222400962,4-Difluoro-3-(pyridin-3-yl)benzeneboronic acid수율 85.1%

시약·촉매·용매 1

HCID 312751,4-Dioxane용매

반응 조건

온도
90 °C

실험 절차

A mixture of 3-(3-bromo-2,6-difluorophenyl)pyridine (2.97 g, 11 mmol), potassium acetate (2.16 g, 22 mmol) and bis(neopentyl glycolato)diboron (2.86 g, 12.7 mmol) in 1,4-dioxane (30 ml) was heated at 90° C. for 16 h. The reaction was cooled, filtered (washing the filter cake with a small quantity of diethyl ether) and the filtrate concentrated in vacuo. The residue was partitioned between diethyl ether (100 ml) and 1M sodium hydroxide (100 ml) and the organics discarded. The aqueous was washed with more diethyl ether and then cooled in an ice-water bath. The pH was adjusted to approximately 6 with 36% hydrochloric acid, and allowed to stand for 1 h. The resulting solid was collected by filtration and dried under vacuum to afford 2,4-difluoro-3-(pyridin-3-yl)benzeneboronic acid (2.2 g, 85%) as a grey solid: m/z (ES+) 236 (M++H).

후처리

  1. temperatureThe reaction was cooled
  2. filtrationfiltered (
  3. washwashing the filter cake with a small quantity of diethyl ether) and the filtrate
  4. concentrationconcentrated in vacuo
  5. customThe residue was partitioned between diethyl ether (100 ml) and 1M sodium hydroxide (100 ml)
  6. washThe aqueous was washed with more diethyl ether
  7. temperaturecooled in an ice-water bath
  8. filtrationThe resulting solid was collected by filtration
  9. customdried under vacuum

출처 및 근거

ORD 기록
ord-55487be94dd14405850fedc9b86e69d3
출처 데이터셋
uspto-grants-2005_05
특허 번호
US06900215B2

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