Potassium Carbonate → 4-(3-Bromo-furan-2-yl)-pyridine

HRID 271509노트

반응식

HRID 271509 반응식
Br[C:2]1[O:3][CH:4]=[CH:5][C:6]=1[Br:7].[N:8]1[CH:13]=[CH:12][C:11](B(O)O)=[CH:10][CH:9]=1.C(=O)([O-])[O-].[K+].[K+].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>COCCOC.O.C([O-])(=O)C.[Pd+2].C([O-])(=O)C>[Br:7][C:6]1[CH:5]=[CH:4][O:3][C:2]=1[C:11]1[CH:12]=[CH:13][N:8]=[CH:9][CH:10]=1

참가 물질

8

반응물 4

HCID 11430Potassium CarbonateHCID 11776TriphenylphosphineHCID 2734379(Pyridin-4-yl)boronic acidHCID 70215012,3-Dibromofuran

생성물 1

HCID 157218314-(3-Bromo-furan-2-yl)-pyridine수율 54%

시약·촉매·용매 3

HCID 167845palladium(II) acetate촉매HCID 962Water용매HCID 80711,2-Dimethoxyethane용매

실험 절차

A degassed mixture of 2,3-dibromofuran (11.3 g, 50 mmol), 4-pyridyl boronic acid (M. Lamothe et al, J. Med. Chem., 1997, 40, 3542) (6.15 g, 50 mmol) and potassium carbonate (55 g, 0.4 mol) in ethylene glycol dimethyl ether (300 ml) and water (150 ml) was treated with triphenylphosphine (1.31 g, 5 mmol) and palladium acetate (625 mg, 2.5 mmol) then heated under reflux for 18 hours. After cooling to room temperature, the mixture was filtered through filter aid and the filtrate diluted with water and ethyl acetate. The organic phase was separated, washed with water and brine, dried, concentrated in vacuo and the residue purified by silica gel chromatography to give the title compound (6.0 g, 54%); MS(ES+) m/e 224/226 [M+H]+.

후처리

  1. temperaturethen heated
  2. temperatureunder reflux for 18 hours
  3. filtrationthe mixture was filtered
  4. filtrationthrough filter aid
  5. additionthe filtrate diluted with water and ethyl acetate
  6. customThe organic phase was separated
  7. washwashed with water and brine
  8. customdried
  9. concentrationconcentrated in vacuo
  10. customthe residue purified by silica gel chromatography

출처 및 근거

ORD 기록
ord-5e621bab50a446d88380f65519c7033d
출처 데이터셋
uspto-grants-2008_11
특허 번호
US07452906B2

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