Dichloromethane → 3-(5-(5-Acetylthiophen-2-yl)nicotinoyl)-1-methylpyrrolidin-2-one

HRID 76386

反応式

HRID 76386 の反応式
Br[C:2]1[CH:3]=[N:4][CH:5]=[C:6]([CH:16]=1)[C:7]([CH:9]1[CH2:13][CH2:12][N:11]([CH3:14])[C:10]1=[O:15])=[O:8].[C:17]([C:20]1[S:24][C:23](B(O)O)=[CH:22][CH:21]=1)(=[O:19])[CH3:18].C(Cl)Cl>C1(C)C=CC=CC=1.O1CCOCC1.C1(P(C2C=CC=CC=2)[C-]2C=CC=C2)C=CC=CC=1.[C-]1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=C1.[Fe+2]>[C:17]([C:20]1[S:24][C:23]([C:2]2[CH:3]=[N:4][CH:5]=[C:6]([CH:16]=2)[C:7]([CH:9]2[CH2:13][CH2:12][N:11]([CH3:14])[C:10]2=[O:15])=[O:8])=[CH:22][CH:21]=1)(=[O:19])[CH3:18]

参加物

6

反応物 3

HCID 6344DichloromethaneHCID 4143377(5-Acetylthiophen-2-yl)boronic acidHCID 140613713-(5-Bromopyridine-3-carbonyl)-1-methylpyrrolidin-2-one

生成物 1

HCID 715701183-(5-(5-Acetylthiophen-2-yl)nicotinoyl)-1-methylpyrrolidin-2-one収率 50%

試薬・触媒・溶媒 2

HCID 635956Ferrocene-1,1'-bis-(diphenylphosphine)触媒HCID 21840791Dioxane toluene溶媒

反応条件

温度
85 °C

実験手順

A mixture of 3-(5-bromonicotinoyl)-1-methylpyrrolidin-2-one 3 (1 equiv), 5-Acetyl-2-thiopheneboronic acid (1.2 equiv), 1,1′-bis(diphenylphosphino)ferrocene]dichloro palladium(II) complex with DCM (0.1 equiv) and 2M Na2CO3(4 equiv) in toluene/1,4-dioxane(4:1, 15 volumes) was degassed and filled with nitrogen. Then the reaction mixture was heated to 85° C. and maintained for 2 h. After completion of the reaction filtered through Celite bed and washed with ethyl acetate. The combined organic layer was dried over with anhydrous sodium sulfate, filtered and concentrated under reduced pressure to obtain crude residue which was purified by silica-gel column chromatography using 2% MeOH/DCM as an eluent to afford 50% yield of titled compound.

後処理

  1. customwas degassed
  2. additionfilled with nitrogen
  3. temperaturemaintained for 2 h
  4. filtrationAfter completion of the reaction filtered through Celite bed
  5. washwashed with ethyl acetate
  6. dry with materialThe combined organic layer was dried over with anhydrous sodium sulfate
  7. filtrationfiltered
  8. concentrationconcentrated under reduced pressure
  9. customto obtain crude residue which
  10. customwas purified by silica-gel column chromatography

出典と根拠

ORDレコード
ord-bee8575046a648daae173e0b9e6482e5
出典データセット
uspto-grants-2014_09
特許番号
US08835640B1

関連ノート

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