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

HRID 1593440ノート

反応式

HRID 1593440 の反応式
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

参加物

9

反応物 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

生成物 1

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

試薬・触媒・溶媒 4

HCID 167845palladium(II) acetate触媒HCID 702Ethanol溶媒HCID 962Water溶媒HCID 6228Dimethylformamide溶媒

実験手順

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]+.

後処理

  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)

出典と根拠

ORDレコード
ord-13c957e11e474d0baf2da4a2f43d46db
出典データセット
uspto-grants-2007_11
特許番号
US07297694B2

反応ノート

読み込み中…