Toluene → 3-Octyloxy-6-(6-octyloxypyridin-3-yl)pyridazine

HRID 1721581ノート

反応式

HRID 1721581 の反応式
C1(C)C=CC=CC=1.Cl[C:9]1[N:10]=[N:11][C:12]([O:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH3:23])=[CH:13][CH:14]=1.[CH2:24]([O:32][C:33]1[CH:38]=[CH:37][C:36](B(O)O)=[CH:35][N:34]=1)[CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH3:31].C([O-])([O-])=O.[Na+].[Na+]>C(O)C.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.O>[CH2:16]([O:15][C:12]1[N:11]=[N:10][C:9]([C:36]2[CH:35]=[N:34][C:33]([O:32][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH3:31])=[CH:38][CH:37]=2)=[CH:14][CH:13]=1)[CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH3:23]

参加物

8

反応物 4

HCID 1140TolueneHCID 10340Sodium CarbonateHCID 64098503-Chloro-6-(octyloxy)pyridazineHCID 224127982-Octyloxy-5-pyridineboronic acid

生成物 1

HCID 224128013-Octyloxy-6-(6-octyloxypyridin-3-yl)pyridazine

試薬・触媒・溶媒 3

HCID 178418397HCID 178418397、化合物触媒HCID 702Ethanol溶媒HCID 962Water溶媒

実験手順

40 ml of toluene are added under a protective gas to 1.41 g (5.8 mmol) of 3-chloro-6-octyloxypyridazine. A solution of 1.45 g (5.8 mmol) of 2-octyloxy-5-pyridineboronic acid in 20 ml of ethanol, followed by 1.23 g of Na2CO3 and finally 20 ml of water are added. Finally, mg (0.058 mmol) of tetrakis(triphenylphosphine)palladium(0) are added with stirring. The mixture is refluxed for 8 hours and cooled, the phases are separated, the organic phase is washed once with saturated aqueous NaHCO3 solution and dried over MgSO4, and the solvent is removed in vacuo. The residue is chromatographed on SiO2 using CH2Cl2 /ethyl acetate: 20/1. The product obtained can be further purified by recrystallization from n-heptane.

後処理

  1. additionare added
  2. temperatureThe mixture is refluxed for 8 hours
  3. temperaturecooled
  4. customthe phases are separated
  5. washthe organic phase is washed once with saturated aqueous NaHCO3 solution
  6. dry with materialdried over MgSO4
  7. customthe solvent is removed in vacuo
  8. customThe residue is chromatographed on SiO2
  9. customThe product obtained can
  10. custombe further purified by recrystallization from n-heptane

出典と根拠

ORDレコード
ord-ffe6218784ef4a5cbd3ca437a2c209f5
出典データセット
uspto-grants-1996_04
特許番号
US05512207

反応ノート

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