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

HRID 546759
ノート
印刷プレビュー

反応式

HRID 546759 の反応式
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
参加物反応条件実験手順後処理出典と根拠反応ノート

参加物

7

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 3

HCID 80271Tri-o-tolylphosphine触媒
HCID 9811564
Bis(dibenzylideneacetone)palladium
触媒
HCID 6228Dimethylformamide溶媒

反応条件

温度
100 °C

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-f719a0a21da949cd89edbd2cc915c80c
出典データセット
uspto-grants-2011_05
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US07935815B2

反応ノート

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