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Acrylamide → (E)-3-[6-methoxy-5-(4-methyl-1H-imidazol-1-yl)pyridin-2-yl]acrylamide

HRID 546759
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인쇄 미리보기

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HRID 546759 반응식
C(N(CC)CC)C.Br[C:9]1[N:14]=[C:13]([O:15][CH3:16])[C:12]([N:17]2[CH:21]=[C:20]([CH3:22])[N:19]=[CH:18]2)=[CH:11][CH:10]=1.[C:23]([NH2:27])(=[O:26])[CH:24]=[CH2:25]>CN(C)C=O.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd].C1(C)C=CC=CC=1P(C1C=CC=CC=1C)C1C=CC=CC=1C>[CH3:16][O:15][C:13]1[N:14]=[C:9](/[CH:25]=[CH:24]/[C:23]([NH2:27])=[O:26])[CH:10]=[CH:11][C:12]=1[N:17]1[CH:21]=[C:20]([CH3:22])[N:19]=[CH:18]1
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참가 물질

7

반응물 3

HCID 6579AcrylamideHCID 8471TriethylamineHCID 576093006-bromo-2-methoxy-3-(4-methyl-1H-imidazol-1-yl)pyridine

생성물 1

HCID 66839442(E)-3-[6-methoxy-5-(4-methyl-1H-imidazol-1-yl)pyridin-2-yl]acrylamide수율 89.5%

시약·촉매·용매 3

HCID 80271Tri-o-tolylphosphine촉매
HCID 9811564
Bis(dibenzylideneacetone)palladium
촉매
HCID 6228Dimethylformamide용매

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온도
100 °C

실험 절차

Triethylamine (52 ml) was added to a suspension of 6-bromo-2-methoxy-3-(4-methyl-1H-imidazol-1-yl)pyridine (49.8 g), tris(dibenzylideneacetone)dipalladium (0) (5.11 g), tri-o-tolylphosphine (3.41 g) and acrylamide (14.5 g) in N,N-dimethyl formamide (260 ml). The reaction solution was stirred at 100° C. for 50 minutes. The reaction solution was returned to room temperature and then filtered through celite. The filter cake was sequentially washed with N,N-dimethylformamide, methanol, a 50% N,N-dimethylformamide solution and N,N-dimethylformamide. The resulting filtrate was filtered through celite again, and the filtrate was concentrated under reduced pressure. Toluene was added to the residue, and the reaction solution was concentrated again. Toluene and a saturated sodium bicarbonate solution were added to the resulting residue, and the insoluble matter was collected by filtration. The resulting powder was dried under reduced pressure to obtain 42.96 g of the title compound. The property values of the compound are as follows.

후처리

  1. customwas returned to room temperature
  2. filtrationfiltered through celite
  3. washThe filter cake was sequentially washed with N,N-dimethylformamide, methanol
  4. filtrationThe resulting filtrate was filtered through celite again
  5. concentrationthe filtrate was concentrated under reduced pressure
  6. additionToluene was added to the residue
  7. concentrationthe reaction solution was concentrated again
  8. additionToluene and a saturated sodium bicarbonate solution were added to the resulting residue
  9. filtrationthe insoluble matter was collected by filtration
  10. customThe resulting powder was dried under reduced pressure

출처 및 근거

ORD 기록
ord-f719a0a21da949cd89edbd2cc915c80c
출처 데이터셋
uspto-grants-2011_05
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US07935815B2

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