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

HRID 1721581노트

반응식

HRID 1721581 반응식
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]

참가 물질

8

반응물 4

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

생성물 1

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

시약·촉매·용매 3

HCID 178418397HCID 178418397, 화합물촉매HCID 702Ethanol용매HCID 962Water용매

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-ffe6218784ef4a5cbd3ca437a2c209f5
출처 데이터셋
uspto-grants-1996_04
특허 번호
US05512207

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