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Potassium Carbonate → 1-(3-(3-bromo-2-methylimidazo[1,2-a]pyridin-8-yloxymethyl)-2,4-dichlorophenyl]-2-[(E)-3-[6-[(E)-2-(pyridin-4-yl)vinyl]pyridin-3-yl]acryloylaminomethyl]pyrrole

HRID 613625
ノート
印刷プレビュー

反応式

HRID 613625 の反応式
[Cl:1][C:2]1[C:7]([CH2:8][OH:9])=[C:6]([Cl:10])[CH:5]=[CH:4][C:3]=1[N:11]1[CH:15]=[CH:14][CH:13]=[C:12]1[CH2:16][NH:17][C:18](=[O:35])/[CH:19]=[CH:20]/[C:21]1[CH:22]=[N:23][C:24](/[CH:27]=[CH:28]/[C:29]2[CH:34]=[CH:33][N:32]=[CH:31][CH:30]=2)=[CH:25][CH:26]=1.CS(Cl)(=O)=O.[Br:41][C:42]1[N:46]2[CH:47]=[CH:48][CH:49]=[C:50](O)[C:45]2=[N:44][C:43]=1[CH3:52].C(=O)([O-])[O-].[K+].[K+]>CN(C)C=O.O.C(N(CC)CC)C>[Br:41][C:42]1[N:46]2[CH:47]=[CH:48][CH:49]=[C:50]([O:9][CH2:8][C:7]3[C:2]([Cl:1])=[C:3]([N:11]4[CH:15]=[CH:14][CH:13]=[C:12]4[CH2:16][NH:17][C:18](=[O:35])/[CH:19]=[CH:20]/[C:21]4[CH:22]=[N:23][C:24](/[CH:27]=[CH:28]/[C:29]5[CH:30]=[CH:31][N:32]=[CH:33][CH:34]=5)=[CH:25][CH:26]=4)[CH:4]=[CH:5][C:6]=3[Cl:10])[C:45]2=[N:44][C:43]=1[CH3:52]
参加物実験手順後処理出典と根拠反応ノート

参加物

8

反応物 4

HCID 11430Potassium CarbonateHCID 31297Methanesulfonyl chlorideHCID 183218891-(2,4-dichloro-3-hydroxymethylphenyl)-2-[(E)-3-[6-[(E)-2-(pyridin-4-yl)vinyl]pyridin-3-yl]acryloylaminomethyl]pyrroleHCID 183219553-Bromo-8-hydroxy-2-methylimidazo[1,2-a]pyridine

生成物 1

HCID 70255217
1-(3-(3-bromo-2-methylimidazo[1,2-a]pyridin-8-yloxymethyl)-2,4-dichlorophenyl]-2-[(E)-3-[6-[(E)-2-(pyridin-4-yl)vinyl]pyridin-3-yl]acryloylaminomethyl]pyrrole
収率 76.9%

試薬・触媒・溶媒 3

HCID 962Water溶媒HCID 6228Dimethylformamide溶媒HCID 8471Triethylamine溶媒

実験手順

To a solution of 1-(2,4-dichloro-3-hydroxymethylphenyl)-2-[(E)-3-[6-[(E)-2-(pyridin-4-yl)vinyl]pyridin-3-yl]acryloylaminomethyl]pyrrole (70 mg) and triethylamine (28 mg) in N,N-dimethylformamide (1 ml) was added methanesulfonyl chloride (16.7 mg) under ice-cooling, and the mixture was stirred for 30 minutes at the same temperature. To the mixture were added 3-bromo-8-hydroxy-2-methylimidazo[1,2-a]-pyridine (31.4 mg) and potassium carbonate (95.7 mg) at ambient temperature, and the mixture was stirred at the same temperature overnight. Water was added thereto, the resulting precipitates were collected by filtration. The residue was purified by preparative thin layer chromatography (chloroform:methanol=10:1, V/V) to give 1-[3-(3-bromo-2-methylimidazo[1,2-a]pyridin-8-yloxymethyl)-2,4-dichlorophenyl]-2-[(E)-3-[6-[(E)-2-(pyridin-4-yl)vinyl]-pyridin-3-yl]acryloylaminomethyl]pyrrole (76 mg) as yellow amorphous.

後処理

  1. temperaturecooling
  2. stirringthe mixture was stirred at the same temperature overnight
  3. customthe resulting precipitates
  4. filtrationwere collected by filtration
  5. customThe residue was purified by preparative thin layer chromatography (chloroform:methanol=10:1, V/V)

出典と根拠

ORDレコード
ord-17124088613b4d379327f4cda9ca3aec
出典データセット
uspto-grants-1999_12
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US06008229

反応ノート

読み込み中…

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