Triphenylphosphine → 5-(2-Pyridin-4-ylfuran-3-yl)indan-1-one

HRID 1593440노트

반응식

HRID 1593440 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.CC1(C)C(C)(C)OB([C:21]2[CH:22]=[C:23]3[C:27](=[CH:28][CH:29]=2)[C:26](=[O:30])[CH2:25][CH2:24]3)O1.C([O-])(=O)C.[K+].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>CN(C)C=O.C(O)C.O.C([O-])(=O)C.[Pd+2].C([O-])(=O)C>[N:10]1[CH:11]=[CH:12][C:7]([C:3]2[O:4][CH:5]=[CH:6][C:2]=2[C:21]2[CH:22]=[C:23]3[C:27](=[CH:28][CH:29]=2)[C:26](=[O:30])[CH2:25][CH2:24]3)=[CH:8][CH:9]=1

참가 물질

9

반응물 4

HCID 11776TriphenylphosphineHCID 517044Potassium AcetateHCID 157218314-(3-Bromo-furan-2-yl)-pyridineHCID 185417105-(tetramethyl-1,3,2-dioxaborolan-2-yl)-2,3-dihydro-1H-inden-1-one

생성물 1

HCID 694314975-(2-Pyridin-4-ylfuran-3-yl)indan-1-one수율 62%

시약·촉매·용매 4

HCID 167845palladium(II) acetate촉매HCID 702Ethanol용매HCID 962Water용매HCID 6228Dimethylformamide용매

실험 절차

A solution of the product of Example 5 Step 5 (0.22 g, 1 mmol), 5-(4,4,5,5-tetramethyl-[1,3,2]-dioxaborolan-2-yl)indanone (0.25 g, 1 mmol) (WO98/45265) and potassium acetate (294 mg, 3 mmol) in dimethylformamide (2 ml), ethanol (2 ml) and water (2 ml) was treated with palladium (II) acetate (12 mg, 0.05 mmol) and triphenylphosphine (26.2 mg, 0.1 mmol) and heated under reflux for 5 hours. The reaction mixture was cooled to room temperature filtered through celite and concentrated in vacuo. The residue was diluted with ethyl acetate, washed with water and saturated brine, dried (MgSO4) and concentrated in vacuo. The residue was chromatographed on silica gel eluting with hexane/ethyl acetate (1:1) and methanol/ethyl acetate (1:9) to afford the title compound (0.17 g, 62%); MS(ES+) m/e 276 [M+H]+.

후처리

  1. temperatureheated
  2. temperatureunder reflux for 5 hours
  3. filtrationfiltered through celite and
  4. concentrationconcentrated in vacuo
  5. additionThe residue was diluted with ethyl acetate
  6. washwashed with water and saturated brine
  7. dry with materialdried (MgSO4)
  8. concentrationconcentrated in vacuo
  9. customThe residue was chromatographed on silica gel eluting with hexane/ethyl acetate (1:1) and methanol/ethyl acetate (1:9)

출처 및 근거

ORD 기록
ord-13c957e11e474d0baf2da4a2f43d46db
출처 데이터셋
uspto-grants-2007_11
특허 번호
US07297694B2

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