Water → N-methyl-3-[3-(3-pyrazol-1-yl-phenyl)-imidazo[1,2-a]pyridin-7-yl]-benzamide

HRID 383269ノート

反応式

HRID 383269 の反応式
Br[C:2]1[N:6]2[CH:7]=[CH:8][C:9]([C:11]3[CH:12]=[C:13]([CH:18]=[CH:19][CH:20]=3)[C:14]([NH:16][CH3:17])=[O:15])=[CH:10][C:5]2=[N:4][CH:3]=1.[N:21]1([C:26]2[CH:27]=[C:28](B(O)O)[CH:29]=[CH:30][CH:31]=2)[CH:25]=[CH:24][CH:23]=[N:22]1.O.C([O-])([O-])=O.[Na+].[Na+]>COCCOC.Cl[Pd](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1>[CH3:17][NH:16][C:14](=[O:15])[C:13]1[CH:18]=[CH:19][CH:20]=[C:11]([C:9]2[CH:8]=[CH:7][N:6]3[C:2]([C:30]4[CH:29]=[CH:28][CH:27]=[C:26]([N:21]5[CH:25]=[CH:24][CH:23]=[N:22]5)[CH:31]=4)=[CH:3][N:4]=[C:5]3[CH:10]=2)[CH:12]=1

参加物

7

反応物 4

HCID 962WaterHCID 10340Sodium CarbonateHCID 16640530(3-(1H-pyrazol-1-yl)phenyl)boronic acidHCID 684844313-(3-Bromo-imidazo[1,2-a]pyridine-7-yl)-N-methyl-benzamide

生成物 1

HCID 25262355N-methyl-3-[3-(3-pyrazol-1-yl-phenyl)-imidazo[1,2-a]pyridin-7-yl]-benzamide

試薬・触媒・溶媒 2

HCID 178418476HCID 178418476、化合物触媒HCID 80711,2-Dimethoxyethane溶媒

実験手順

3-(3-Bromo-imidazo[1,2-a]pyridine-7-yl)-N-methyl-benzamide (Intermediate EA) (1 eq, 0.303 mmol, 100 mg) and 3-(1H-pyrazolyl)-phenylboronic acid (1.3 eq, 0.394 mmol, 74 mg) are dissolved in DME (3 ml) and water (0.8 ml) and Na2CO3 (3 eq, 0.909 mmol, 96.3 mg) is added. PdCl2(PPh3)2 (0.05 eq, 0.015 mmol, 10.6 mg) is added and the reaction mixture is heated using microwave radiation at 120° C. for 10 min. At the completion of this time the solvent is removed in vacuo and the reaction mixture is purified by flash column chromatography eluting with 9:1 DCM/MeOH to yield N-methyl-3-[3-(3-pyrazol-1-yl-phenyl)-imidazo[1,2-a]pyridin-7-yl]-benzamide as a light brown solid; [M+H]+=395

後処理

  1. temperaturethe reaction mixture is heated
  2. customat 120° C.
  3. customfor 10 min
  4. customAt the completion of this time the solvent is removed in vacuo
  5. customthe reaction mixture is purified by flash column chromatography
  6. washeluting with 9:1 DCM/MeOH

出典と根拠

ORDレコード
ord-b4ef440985944f6ca8d66ed403e850e8
出典データセット
uspto-grants-2013_02
特許番号
US08367662B2

反応ノート

読み込み中…