Triphenylphosphine → 5-(1-Methoxyimino-indan-5-yl)-4-pyridin-4-yl-furan-2-carbaldehyde

HRID 271515노트

반응식

HRID 271515 반응식
Br[C:2]1[CH:3]=[C:4]([CH:19]=[O:20])[O:5][C:6]=1[C:7]1[CH:8]=[C:9]2[C:13](=[CH:14][CH:15]=1)[C:12](=[N:16][O:17][CH3:18])[CH2:11][CH2:10]2.C([Sn](CCCC)(CCCC)[C:26]1[CH:31]=[CH:30][N:29]=[CH:28][CH:27]=1)CCC.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>C1(C)C=CC=CC=1.C([O-])(=O)C.[Pd+2].C([O-])(=O)C>[CH3:18][O:17][N:16]=[C:12]1[C:13]2[C:9](=[CH:8][C:7]([C:6]3[O:5][C:4]([CH:19]=[O:20])=[CH:3][C:2]=3[C:26]3[CH:31]=[CH:30][N:29]=[CH:28][CH:27]=3)=[CH:15][CH:14]=2)[CH2:10][CH2:11]1

참가 물질

6

반응물 3

HCID 11776TriphenylphosphineHCID 27373184-(Tri-n-butylstannyl)pyridineHCID 867607594-Bromo-5-(1-methoxyimino-indan-5-yl)-furan-2-carbaldehyde

생성물 1

HCID 867607605-(1-Methoxyimino-indan-5-yl)-4-pyridin-4-yl-furan-2-carbaldehyde수율 69%

시약·촉매·용매 2

HCID 167845palladium(II) acetate촉매HCID 1140Toluene용매

실험 절차

A degassed mixture of the product of Step 4 (2.0 g, 6.0 mmol) and 4-tributylstannylpyridine (2.5 g, 6.8 mmol) in toluene (100 ml) was treated with triphenylphosphine (156 mg, 0.6 mmol) and palladium acetate (67 mg, 0.3 mmol) then heated under reflux for 60 hours. The reaction mixture was concentrated in vacuo and the product purified by silica gel chromatography eluting with ethyl acetate/hexane (1:1) and then ethyl acetate to give the title compound (1.37 g, 69%); MS(ES+) m/e 333 [M+H]+.

후처리

  1. temperaturethen heated
  2. temperatureunder reflux for 60 hours
  3. concentrationThe reaction mixture was concentrated in vacuo
  4. customthe product purified by silica gel chromatography
  5. washeluting with ethyl acetate/hexane (1:1)

출처 및 근거

ORD 기록
ord-d59478a4e454451788f17817b8af18ac
출처 데이터셋
uspto-grants-2008_11
특허 번호
US07452906B2

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