Ethanol → HCID 20095007, compound

HRID 1770184Notes

Reaction equation

HRID 1770184 reaction equation
[CH2:1]([CH:9]1[CH2:17][C:16]2[C:11](=[CH:12][CH:13]=[C:14](B(O)O)[CH:15]=2)[CH2:10]1)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH3:8].Cl[C:22]1[N:23]=[N:24][C:25]([CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][CH3:35])=[CH:26][CH:27]=1.C(O)C.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:9]1[CH2:17][C:16]2[C:11](=[CH:12][CH:13]=[C:14]([C:22]3[N:23]=[N:24][C:25]([CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][CH3:35])=[CH:26][CH:27]=3)[CH:15]=2)[CH2:10]1)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH3:8]

Participants

7

Reactant 4

HCID 702EthanolHCID 10340Sodium CarbonateHCID 20095030HCID 20095030, compoundHCID 220990862-Octylindane-5-boronic acid

Product 1

HCID 20095007HCID 20095007, compoundYield 73.1%

Reagents, catalysts & solvents 2

HCID 11979704Tetrakis(triphenylphosphine)palladiumCatalystHCID 241BenzeneSolvent

Procedure

Then, 0.82 g (3.0 mM) of 2-octylindan-5-boronic acid, 0.68 g (3.0 mM) of 3-chloro-6-octylpyridazine, 2 ml of ethanol, 4 ml of benzene, 4 ml of 2M-sodium carbonate aqueous solution and 0.12 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/methanol) to obtain 0.92 g (2.19 mM) of 2-octyl-5-(6-octylpyridazine-3-yl)indan (Yield: 73%). ##STR318##

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/methanol)

Sources & evidence

ORD record
ord-68e29880420b46a09d5c6fc8bb4add3b
Source dataset
uspto-grants-1995_01
Patent number
US05385692

Reaction notes

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