Ethanol → HCID 20095063, compound

HRID 1770186Notes

Reaction equation

HRID 1770186 reaction equation
[CH2:1]([CH:7]1[CH2:15][C:14]2[C:9](=[CH:10][CH:11]=[C:12](B(O)O)[CH:13]=2)[CH2:8]1)[CH2:2][CH2:3][CH2:4][CH2:5][CH3:6].Cl[C:20]1[N:21]=[N:22][C:23](Cl)=[CH:24][CH:25]=1.[CH2:27](O)[CH3:28].C(=O)([O-])[O-].[Na+].[Na+]>[Pd].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1C=CC=CC=1>[CH2:1]([CH:7]1[CH2:15][C:14]2[C:9](=[CH:10][CH:11]=[C:12]([C:20]3[N:21]=[N:22][C:23]([C:12]4[CH:13]=[C:14]5[C:9](=[CH:10][CH:11]=4)[CH2:8][CH:7]([CH2:1][CH2:2][CH2:3][CH2:4][CH2:27][CH3:28])[CH2:15]5)=[CH:24][CH:25]=3)[CH:13]=2)[CH2:8]1)[CH2:2][CH2:3][CH2:4][CH2:5][CH3:6]

Participants

7

Reactant 4

HCID 702EthanolHCID 10340Sodium CarbonateHCID 673313,6-DichloropyridazineHCID 20095048HCID 20095048, compound

Product 1

HCID 20095063HCID 20095063, compoundYield 79%

Reagents, catalysts & solvents 2

HCID 11979704Tetrakis(triphenylphosphine)palladiumCatalystHCID 241BenzeneSolvent

Procedure

0.74 g (3.0 mM) of 2-hexylindan-5-boronic acid, 0.22 g (1.5 mM) of 3,6-dichloropyridazine, 2 ml of ethanol, 4 ml of benzene, 4 ml of 2M-sodium carbonate aqueous solution and 0.21 g of tetrakis (triphenylphosphine) palladium (O) were mixed and heat-refluxed for 2 hours under stirring. After the reaction, the reaction mixture was poured into ice water to precipitate a crystal. The crystal was recovered by filtration under reduced pressure and purified by silica gel column chromatography (eluent: toluene) and recrystallized from a mixture solvent (toluene/ethyl acetate) to obtain 0.57 g (1.19 mM) of 3,6-bis(2-hexylindan-5-yl)pyridazine (Yield: 79%). ##STR323##

Workup

  1. temperatureheat-refluxed for 2 hours
  2. customAfter the reaction
  3. customto precipitate a crystal
  4. filtrationThe crystal was recovered by filtration under reduced pressure
  5. custompurified by silica gel column chromatography (eluent: toluene)
  6. customrecrystallized from a mixture solvent (toluene/ethyl acetate)

Sources & evidence

ORD record
ord-eae9af6646d5478f9a0b861e10e9440f
Source dataset
uspto-grants-1995_01
Patent number
US05385692

Reaction notes

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