Sodium Carbonate → HCID 23624542、化合物

HRID 389044

反応式

HRID 389044 の反応式
Cl[C:2]1[N:3]=[N:4][C:5]([N:8]2[CH2:13][CH2:12][N:11]([CH:14]3[CH2:16][CH2:15]3)[CH2:10][CH2:9]2)=[CH:6][CH:7]=1.C(=O)([O-])[O-].[Na+].[Na+].[CH2:23]1[O:31][C:30]2[CH:29]=[CH:28][C:27](B(O)O)=[CH:26][C:25]=2[O:24]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.C(#N)C>[O:24]1[C:25]2[CH:26]=[CH:27][C:28]([C:2]3[N:3]=[N:4][C:5]([N:8]4[CH2:13][CH2:12][N:11]([CH:14]5[CH2:16][CH2:15]5)[CH2:10][CH2:9]4)=[CH:6][CH:7]=3)=[CH:29][C:30]=2[O:31][CH2:23]1

参加物

6

反応物 3

HCID 10340Sodium CarbonateHCID 2734371(2H-1,3-benzodioxol-5-yl)boronic acidHCID 614441503-Chloro-6-(4-cyclopropylpiperazin-1-yl)pyridazine

生成物 1

HCID 23624542HCID 23624542、化合物

試薬・触媒・溶媒 2

HCID 178418476HCID 178418476、化合物触媒HCID 6342Acetonitrile溶媒

反応条件

温度
80 °C

実験手順

3-Chloro-6-(4-cyclopropylpiperazin-1-yl)pyridazine (8.0 g, 33.5 mmol), acetonitrile (100 mL), 1 M sodium carbonate solution (100.5 mL, 100.5 mmol) and bis(triphenylphosphine)palladium(II) chloride (1.17 g, 1.67 mmol) were mixed and degassed in vacuo under nitrogen. 3,4-Methylenedioxybenzeneboronic acid (8.34 g, 50.3 mmol) was added and the mixture was heated to 80° C. for 16 h. The precipitated product was filtered and washed with acetonitrile and water, and dried in vacuo. The solid was suspended in methanol (500 mL) and 2,2 equivalents of a 4M HCl in dioxane solution was added. The formed solution was filtered, concentrated in vacuo and acetonitrile (100 mL) was added. The suspension was stirred for 1 h, filtered and the solid dried in vacuo to yield 3-(1,3-benzodioxol-5-yl)-6-(4-cyclopropylpiperazin-1-yl)pyridazine as a yellow powder, 11.4 g, 86%.

後処理

  1. customdegassed in vacuo under nitrogen
  2. filtrationThe precipitated product was filtered
  3. washwashed with acetonitrile and water
  4. customdried in vacuo
  5. addition2,2 equivalents of a 4M HCl in dioxane solution was added
  6. filtrationThe formed solution was filtered
  7. concentrationconcentrated in vacuo and acetonitrile (100 mL)
  8. additionwas added
  9. filtrationfiltered
  10. customthe solid dried in vacuo

出典と根拠

ORDレコード
ord-98a5652ec5814fc58020b88c343717e9
出典データセット
uspto-grants-2013_02
特許番号
US08378097B2

関連ノート

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