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Sodium Carbonate → N-[4-methoxy-3-(4-methyl-1-piperazinyl)phenyl]-2-(4-pyridyl)-3-methoxythiophene-4-carboxamide

HRID 355747
ノート
印刷プレビュー

反応式

HRID 355747 の反応式
Br[C:2]1[S:3][CH:4]=[C:5]([C:9]([NH:11][C:12]2[CH:17]=[CH:16][C:15]([O:18][CH3:19])=[C:14]([N:20]3[CH2:25][CH2:24][N:23]([CH3:26])[CH2:22][CH2:21]3)[CH:13]=2)=[O:10])[C:6]=1[O:7][CH3:8].[N:27]1[CH:32]=[CH:31][C:30](B(O)O)=[CH:29][CH:28]=1.C(=O)([O-])[O-].[Na+].[Na+]>O.COCCOC.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>[CH3:19][O:18][C:15]1[CH:16]=[CH:17][C:12]([NH:11][C:9]([C:5]2[C:6]([O:7][CH3:8])=[C:2]([C:30]3[CH:31]=[CH:32][N:27]=[CH:28][CH:29]=3)[S:3][CH:4]=2)=[O:10])=[CH:13][C:14]=1[N:20]1[CH2:25][CH2:24][N:23]([CH3:26])[CH2:22][CH2:21]1
参加物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 10340Sodium Carbonate2 回HCID 2734379(Pyridin-4-yl)boronic acidHCID 189406682-Bromo-N-[4-methoxy-3-(4-methyl-1-piperazinyl)phenyl]-3-methoxythiophene-4-carboxamide

生成物 1

HCID 22459332N-[4-methoxy-3-(4-methyl-1-piperazinyl)phenyl]-2-(4-pyridyl)-3-methoxythiophene-4-carboxamide

試薬・触媒・溶媒 3

HCID 178418397
HCID 178418397、化合物
触媒
HCID 962Water溶媒
HCID 80711,2-Dimethoxyethane溶媒

実験手順

2-Bromo-N-[4-methoxy-3-(4-methyl- 1-piperazinyl)phenyl]-3-methoxythiophene-4-carboxamide (0.20 g;0.45 mmol) was stirred with 4-pyridylboronic acid (0.056 g;0.45 mmol), tetrakis(triphenylphosphine)palladium(0) (0.024 g) and anhydrous sodium carbonate (0.053 g;0.50 mmol) in water (5 ml) and DME (5 ml) and the whole heated at reflux under Ar (18 hours). The reaction mixture was poured into 10% Na2CO3 (aq) (20 ml) and extracted into CHCl3. The organic extracts were combined, dried over Na2SO4, filtered and the filtrate evaporated in vacuo to a brown gum. The gum was purified by flash silica-gel chromatography and eluted with 4%MeOH/CHCl3 to yield a orange gum (0.088;44%).

後処理

  1. temperaturethe whole heated
  2. temperatureat reflux under Ar (18 hours)
  3. extractionextracted into CHCl3
  4. dry with materialdried over Na2SO4
  5. filtrationfiltered
  6. customthe filtrate evaporated in vacuo to a brown gum
  7. customThe gum was purified by flash silica-gel chromatography
  8. washeluted with 4%MeOH/CHCl3
  9. customto yield a orange gum (0.088;44%)

出典と根拠

ORDレコード
ord-d15e21b9974c4cc2a1ce18e1771982cd
出典データセット
uspto-grants-1998_11
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US05834471

反応ノート

読み込み中…

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