Hydrochloric Acid → 2-Chloro-6-propylimidazo[1,2-b]pyridazine

HRID 969726

反応式

HRID 969726 の反応式
[Br-].[CH2:2]([Zn+])[CH2:3][CH3:4].O1CCCC1.[Cl:11][C:12]1[N:13]=[C:14]2[CH:19]=[CH:18][C:17](Cl)=[N:16][N:15]2[CH:21]=1.Cl>C1(C)C=CC=CC=1.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.O>[Cl:11][C:12]1[N:13]=[C:14]2[CH:19]=[CH:18][C:17]([CH2:2][CH2:3][CH3:4])=[N:16][N:15]2[CH:21]=1

参加物

8

反応物 4

HCID 313Hydrochloric AcidHCID 8028TetrahydrofuranHCID 144223582,6-Dichloroimidazo[1,2-b]pyridazineHCID 178455869HCID 178455869、化合物

生成物 1

HCID 230280952-Chloro-6-propylimidazo[1,2-b]pyridazine

試薬・触媒・溶媒 3

HCID 178418476HCID 178418476、化合物触媒HCID 962Water溶媒HCID 1140Toluene溶媒

反応条件

温度
80 °C

実験手順

Under a nitrogen stream, a solution of n-propylzinc bromide in tetrahydrofuran (0.5 M, 7.98 ml, 3.99 mmol) was diluted with toluene (5.0 ml), and 2,6-dichloroimidazo[1,2-b]pyridazine (0.50 g, 2.66 mmol) and bis(triphenylphosphine)palladium(II) dichloride (0.19 g, 0.27 mmol) were added thereto, and the reaction mixture was stirred for 2 hours at 80° C. After cooling, to the reaction mixture was added cold water (50 ml), acidified with dilute hydrochloric acid, extracted with ethyl acetate, and the extracts were washed with dilute hydrochloric acid, a saturated saline, an aqueous saturated sodium bicarbonate solution and a saturated saline in this order. The resulting organic layer was dried over anhydrous magnesium sulfate, filtrated and concentrated. The concentrated residue was purified by silica gel column chromatography (ethyl acetate:hexane=3:7) to give the title compound as white crystals. The yield was 0.31 g (59.6%).

後処理

  1. additionwere added
  2. temperatureAfter cooling, to the reaction mixture
  3. extractionextracted with ethyl acetate
  4. washthe extracts were washed with dilute hydrochloric acid
  5. dry with materialThe resulting organic layer was dried over anhydrous magnesium sulfate
  6. filtrationfiltrated
  7. concentrationconcentrated
  8. customThe concentrated residue was purified by silica gel column chromatography (ethyl acetate:hexane=3:7)

出典と根拠

ORDレコード
ord-f38b27477ba748549e40efb5c42ed7b5
出典データセット
uspto-grants-2007_12
特許番号
US07307165B2

関連ノート

読み込み中…