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

HRID 1593424
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HRID 1593424 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 61%

시약·촉매·용매 3

HCID 167845
palladium(II) acetate
촉매
HCID 962Water용매2회
HCID 80711,2-Dimethoxyethane용매

실험 절차

A solution of the product of Step 5 (1.2 g, 5.4 mmol ) and the product of Step 6 (2.2 g, 6.4 mmol ) in 1,2-dimethoxyethane (40 ml) and water (20 ml) was treated with potassium carbonate (6.0 g, 43.2 mmol), palladium acetate (0.06 g, 0.27 mmol) and triphenylphosphine (0. 14 g, 0.54 mmol) and heated under reflux for 1.5 hours. After cooling to room temperature, the reaction mixture was poured into water, extracted into ethyl acetate, dried (MgSO4) and concentrated in vacuo. The residue was chromatographed on silica gel eluting with ethyl acetate to afford the title compound (1.0 g, 61%); MS(ES+) m/e 305 [M+H]+.

후처리

  1. temperatureheated
  2. temperatureunder reflux for 1.5 hours
  3. extractionextracted into ethyl acetate
  4. dry with materialdried (MgSO4)
  5. concentrationconcentrated in vacuo
  6. customThe residue was chromatographed on silica gel eluting with ethyl acetate

출처 및 근거

ORD 기록
ord-60382491e55543e58c66107ec9886fff
출처 데이터셋
uspto-grants-2007_11
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US07297694B2

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