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

HRID 407168

반응식

HRID 407168 반응식
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.C([O-])([O-])=O.[Na+].[Na+]>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]

참가 물질

7

반응물 4

HCID 6344DichloromethaneHCID 10340Sodium CarbonateHCID 4143377(5-Acetylthiophen-2-yl)boronic acidHCID 140613713-(5-Bromopyridine-3-carbonyl)-1-methylpyrrolidin-2-one

생성물 1

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

시약·촉매·용매 2

HCID 635956Ferrocene-1,1'-bis-(diphenylphosphine)촉매HCID 21840791Dioxane toluene용매

반응 조건

온도
85 °C

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-bbe03d7274b04b19b844bded081d50a4
출처 데이터셋
uspto-grants-2014_06
특허 번호
US08754228B2

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