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

HRID 1721581
Notes
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Reaction equation

HRID 1721581 reaction equation
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]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

8

Reactant 4

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

Product 1

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

Reagents, catalysts & solvents 3

HCID 178418397
HCID 178418397, compound
Catalyst
HCID 702EthanolSolvent
HCID 962WaterSolvent

Procedure

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.

Workup

  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

Sources & evidence

ORD record
ord-ffe6218784ef4a5cbd3ca437a2c209f5
Source dataset
uspto-grants-1996_04
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US05512207

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes