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Potassium Carbonate → 5-(2-Pyridin-4-ylfuran-3-yl)indan-1-one O-methyl oxime

HRID 271510
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인쇄 미리보기

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HRID 271510 반응식
Br[C:2]1[CH:6]=[CH:5][O:4][C:3]=1[C:7]1[CH:12]=[CH:11][N:10]=[CH:9][CH:8]=1.[CH3:13][O:14][N:15]=[C:16]1[C:24]2[C:19](=[CH:20][C:21](B(O)O)=[CH:22][CH:23]=2)[CH2:18][CH2:17]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>[CH3:13][O:14][N:15]=[C:16]1[C:24]2[C:19](=[CH:20][C:21]([C:2]3[CH:6]=[CH:5][O:4][C:3]=3[C:7]3[CH:12]=[CH:11][N:10]=[CH:9][CH:8]=3)=[CH:22][CH:23]=2)[CH2:18][CH2:17]1
참가 물질실험 절차후처리출처 및 근거반응 노트

참가 물질

8

반응물 4

HCID 11430Potassium CarbonateHCID 11776TriphenylphosphineHCID 157218314-(3-Bromo-furan-2-yl)-pyridineHCID 734146811-Methoxyimino-indan-5-boronic acid

생성물 1

HCID 865954135-(2-Pyridin-4-ylfuran-3-yl)indan-1-one O-methyl oxime수율 79.4%

시약·촉매·용매 3

HCID 167845
palladium(II) acetate
촉매
HCID 962Water용매
HCID 80711,2-Dimethoxyethane용매

실험 절차

A degassed mixture of the product of Step 3 (2.7 g, 12 mmol), the product of Step 2 (2.5 g, 12 mmol) and potassium carbonate (13.2 g, 96 mmol) in ethylene glycol dimethyl ether (70 ml) and water (30 ml) was treated with triphenylphosphine (314 mg, 1.2 mmol) and palladium acetate (135 mg, 0.6 mmol), then heated under reflux for 1 hour. 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 (2.9 g, 74%); MS(ES+) m/e 305 [M+H]+.

후처리

  1. temperatureheated
  2. temperatureunder reflux for 1 hour
  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-4ce08cfbfb2647d0a6b5584375faaf5a
출처 데이터셋
uspto-grants-2008_11
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US07452906B2

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