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

HRID 271515ノート

反応式

HRID 271515 の反応式
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

参加物

6

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 2

HCID 167845palladium(II) acetate触媒HCID 1140Toluene溶媒

実験手順

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]+.

後処理

  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)

出典と根拠

ORDレコード
ord-d59478a4e454451788f17817b8af18ac
出典データセット
uspto-grants-2008_11
特許番号
US07452906B2

反応ノート

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