Water → 3-[3-(2-Chloro-pyridin-4-yl)-imidazo[1,2-b]pyridazin-7-yl]-N-methyl-benzamide

HRID 1097302ノート

反応式

HRID 1097302 の反応式
Br[C:2]1[N:6]2[N: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.[Cl:21][C:22]1[CH:27]=[C:26](B(O)O)[CH:25]=[CH:24][N:23]=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>[Cl:21][C:22]1[CH:27]=[C:26]([C:2]2[N:6]3[N:7]=[CH:8][C:9]([C:11]4[CH:12]=[C:13]([CH:18]=[CH:19][CH:20]=4)[C:14]([NH:16][CH3:17])=[O:15])=[CH:10][C:5]3=[N:4][CH:3]=2)[CH:25]=[CH:24][N:23]=1

参加物

7

反応物 4

HCID 962WaterHCID 10340Sodium CarbonateHCID 51515952-Chloropyridine-4-boronic acidHCID 444734593-(3-Bromo-imidazo-[1,2-b]-pyridazin-7-yl)-N-methyl-benzamide2 回

生成物 1

HCID 444734603-[3-(2-Chloro-pyridin-4-yl)-imidazo[1,2-b]pyridazin-7-yl]-N-methyl-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

To a mixture of 3-(3-Bromo-imidazo-[1,2-b]-pyridazin-7-yl)-N-methyl-benzamide (Intermediate A) (1 eq, 0.353 mmol, 117 mg) and 2-chloropyridine-4-boronic acid (1.2 eq, 0.424 mmol, 66.7 mg) in DME (3 ml) are added water (1 ml) and Na2CO3 (2 eq, 0.707 mmol, 87.6 mg). PdCl2(PPh3)2 (0.1 eq, 0.035 mmol, 24.8 mg) is then 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 3-[3-(2-Chloro-pyridin-4-yl)-imidazo[1,2-b]pyridazin-7-yl]-N-methyl-benzamide as a yellow solid; [M+H]+=364

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-f86c9039d8cf437c85e6f0bada8011d2
出典データセット
uspto-grants-2012_03
特許番号
US08143253B2

反応ノート

読み込み中…