Sodium Carbonate → 6-Chloro-3-(2-chloro-pyridin-4-yl)-imidazo[1,2-a]pyridine

HRID 383312ノート

反応式

HRID 383312 の反応式
Br[C:2]1[N:6]2[CH:7]=[C:8]([Cl:11])[CH:9]=[CH:10][C:5]2=[N:4][CH:3]=1.[Cl:12][C:13]1[CH:18]=[C:17](B(O)O)[CH:16]=[CH:15][N:14]=1.C([O-])([O-])=O.[Na+].[Na+]>O1CCOCC1.O.C1(C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)[Pd][P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1>[Cl:11][C:8]1[CH:9]=[CH:10][C:5]2[N:6]([C:2]([C:17]3[CH:16]=[CH:15][N:14]=[C:13]([Cl:12])[CH:18]=3)=[CH:3][N:4]=2)[CH:7]=1

参加物

7

反応物 3

HCID 10340Sodium CarbonateHCID 51515952-Chloropyridine-4-boronic acidHCID 457900423-Bromo-6-chloroimidazo[1,2-a]pyridine

生成物 1

HCID 866443446-Chloro-3-(2-chloro-pyridin-4-yl)-imidazo[1,2-a]pyridine

試薬・触媒・溶媒 3

HCID 178419050HCID 178419050、化合物触媒HCID 962Water溶媒2 回HCID 312751,4-Dioxane溶媒

反応条件

温度
100 °C

実験手順

To a solution of 3-bromo-6-chloro-imidazo[1,2-a]pyridine (1 eq, 18.1 mmol, 4.2 g), 2-chloropyridin-4-yl boronic acid (1.05 eq, 19 mmol, 3 g), Na2CO3 (2 eq, 36.2 mmol, 3.84 g) in dioxane (30 ml) and water (10 ml), under an inert atmosphere of argon is added bis(triphenylphosphine)palladium II chloride (1.23 g). The reaction mixture is heated at 100° C. for 16 hours. The mixture is diluted with H2O (50 ml) and extracted with EtOAc. The combined organic portions are washed with brine, dried (MgSO4) and concentrated in vacuo. The residue is purified by flash chromatography on silica eluting with 0-50% EtOAc in iso-hexane to afford the title compound; [M+H]+=264 (266).

後処理

  1. extractionextracted with EtOAc
  2. washThe combined organic portions are washed with brine
  3. dry with materialdried (MgSO4)
  4. concentrationconcentrated in vacuo
  5. customThe residue is purified by flash chromatography on silica eluting with 0-50% EtOAc in iso-hexane

出典と根拠

ORDレコード
ord-ca169e7cd1ac457d8b4a67956b0cf0f8
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…