Ethanol → HCID 22412654, compound

HRID 1721582Notes

Reaction equation

HRID 1721582 reaction equation
[CH2:1]([O:11][C:12]1[CH:17]=[CH:16][C:15](B(O)O)=[CH:14][N:13]=1)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH3:10].Cl[C:22]1[N:23]=[N:24][C:25](Cl)=[CH:26][CH:27]=1.[C:29](=[O:32])([O-])[O-].[Na+].[Na+].[CH2:35](O)[CH3:36]>C1(C)C=CC=CC=1.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>[CH2:1]([O:11][C:12]1[CH:17]=[CH:16][C:15]([C:22]2[N:23]=[N:24][C:25]([C:17]3[CH:16]=[CH:15][C:14]([O:32][CH2:29][CH2:7][CH2:6][CH2:5][CH2:4][CH2:3][CH2:2][CH2:1][CH2:35][CH3:36])=[N:13][CH:12]=3)=[CH:26][CH:27]=2)=[CH:14][N:13]=1)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH3:10]

Participants

8

Reactant 4

HCID 702EthanolHCID 10340Sodium CarbonateHCID 673313,6-DichloropyridazineHCID 22412900HCID 22412900, compound

Product 1

HCID 22412654HCID 22412654, compoundYield 99.5%

Reagents, catalysts & solvents 3

HCID 178418397HCID 178418397, compoundCatalystHCID 962WaterSolventHCID 1140TolueneSolvent

Procedure

1.6 g (5.73 mmol) of 2-decyloxypyridin-5-boronic acid, 0.28 g (1.91 mmol) of 3,6-dichloropyridazine, 0.03 g (0.024 mmol) of tetrakis(triphenylphosphine)palladium(0) and 0.97 g (9.17 mmol) of sodium carbonate are heated at 80° C. for 24 hours in 30 ml of toluene, 20 ml of ethanol and 10 ml of water. The palladium catalyst is subsequently separated from the reaction mixture by filtration at 80° C. The aqueous lower phase of the reaction mixture is separated off at 80° C., and the organic phase is then freed from solvents in a rotary evaporator and dried in a high vacuum. The crude product obtained in this way is chromatographed on silica gel using dichloromethane/ethyl acetate=20/1 and subsequently recrystallized from acetonitrile, giving 0.38 g of 3,6-bis(2-decyloxypyridin-5-yl)pyridazine (99.5% according to HPLC).

Workup

  1. customThe palladium catalyst is subsequently separated from the reaction mixture by filtration at 80° C
  2. customThe aqueous lower phase of the reaction mixture is separated off at 80° C.
  3. customthe organic phase is then freed from solvents in a rotary evaporator
  4. customdried in a high vacuum
  5. customThe crude product obtained in this way
  6. customis chromatographed on silica gel
  7. customsubsequently recrystallized from acetonitrile

Sources & evidence

ORD record
ord-24552e86067e42438e2db7cdfd222423
Source dataset
uspto-grants-1996_04
Patent number
US05512207

Reaction notes

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