Dimethylformamide → Ethyl 2-(6-cyano-2-oxoquinolin-1(2h)-yl)acetate

HRID 2098055

反応式

HRID 2098055 の反応式
Br[C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[N:8]([CH2:12][C:13]([O:15][CH2:16][CH3:17])=[O:14])[C:7](=[O:18])[CH:6]=[CH:5]2.C(OCC)(=O)C.[CH3:25][N:26](C)C=O>O.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[C:25]([C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[N:8]([CH2:12][C:13]([O:15][CH2:16][CH3:17])=[O:14])[C:7](=[O:18])[CH:6]=[CH:5]2)#[N:26]

参加物

6

反応物 3

HCID 6228DimethylformamideHCID 8857Ethyl AcetateHCID 68786198ethyl 2-(6-bromo-2-oxoquinolin-1(2H)-yl)acetate

生成物 1

HCID 68786957Ethyl 2-(6-cyano-2-oxoquinolin-1(2h)-yl)acetate収率 38%

試薬・触媒・溶媒 2

HCID 178418397HCID 178418397、化合物触媒HCID 962Water溶媒

実験手順

Ethyl 2-(6-bromo-2-oxoquinolin-1(2H)-yl)acetate (2.37 g, 7.64 mmol)cuprous cyanide (8.87 g, 99.0 mmol), and tetrakis(triphenylphosphine)palladium(0) (3.50 g, 3.03 mmol) in dimethylforamide (100 ml) was placed into a preheated oil bath at 140° C. After stirring for 24 h, the solution was diluted with water and extracted with ethyl acetate. The combined organic extracts were dried over magnesium sulfate, filtered, and concentrated under reduced pressure. The residue was flash chromatographed with 9:1, 4:1, 7:3, and 3:2 methylene chloride:ethyl acetate as the eluant to afford 0.74 g (38% yield) of ethyl 2-(6-cyano-2-oxoquinolin-1(2H)-yl)acetate. Method [7] retention time 2.87 min by HPLC (M+257).

後処理

  1. extractionextracted with ethyl acetate
  2. dry with materialThe combined organic extracts were dried over magnesium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated under reduced pressure
  5. customchromatographed with 9:1, 4:1, 7:3, and 3:2 methylene chloride

出典と根拠

ORDレコード
ord-76581d33bd0c4795b9626d4cd5a88f36
出典データセット
uspto-grants-2013_05
特許番号
US08450363B2

関連ノート

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