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

HRID 1593424
ノート
印刷プレビュー

反応式

HRID 1593424 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.[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
参加物実験手順後処理出典と根拠反応ノート

参加物

8

反応物 4

HCID 11430Potassium CarbonateHCID 11776TriphenylphosphineHCID 157218314-(3-Bromo-furan-2-yl)-pyridineHCID 734146811-Methoxyimino-indan-5-boronic acid

生成物 1

HCID 865954135-(2-Pyridin-4-ylfuran-3-yl)indan-1-one O-methyl oxime収率 61%

試薬・触媒・溶媒 3

HCID 167845
palladium(II) acetate
触媒
HCID 962Water溶媒2 回
HCID 80711,2-Dimethoxyethane溶媒

実験手順

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]+.

後処理

  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

出典と根拠

ORDレコード
ord-60382491e55543e58c66107ec9886fff
出典データセット
uspto-grants-2007_11
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US07297694B2

反応ノート

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