Dichloromethane → 2-Fluoro-6-octyloxy-3-[4-(4-octyloxyphenyl)phenyl]pyridine

HRID 1780559

Reaction equation

HRID 1780559 reaction equation
[F:1][C:2]1[C:7](B(O)O)=[CH:6][CH:5]=[C:4]([O:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH3:19])[N:3]=1.Br[C:21]1[CH:26]=[CH:25][C:24]([C:27]2[CH:32]=[CH:31][C:30]([O:33][CH2:34][CH2:35][CH2:36][CH2:37][CH2:38][CH2:39][CH2:40][CH3:41])=[CH:29][CH:28]=2)=[CH:23][CH:22]=1.C(=O)([O-])[O-].[Na+].[Na+].ClCCl>C(O)C.C1C=CC=CC=1.O.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>[F:1][C:2]1[C:7]([C:21]2[CH:22]=[CH:23][C:24]([C:27]3[CH:28]=[CH:29][C:30]([O:33][CH2:34][CH2:35][CH2:36][CH2:37][CH2:38][CH2:39][CH2:40][CH3:41])=[CH:31][CH:32]=3)=[CH:25][CH:26]=2)=[CH:6][CH:5]=[C:4]([O:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH3:19])[N:3]=1

Participants

9

Reactant 4

HCID 6344DichloromethaneHCID 10340Sodium CarbonateHCID 28017871-Bromo-4-(4-octoxyphenyl)benzeneHCID 190469402-Fluoro-6-octyloxypyridine-3-boronic acid

Product 1

HCID 190469732-Fluoro-6-octyloxy-3-[4-(4-octyloxyphenyl)phenyl]pyridineYield 13.2%

Reagents, catalysts & solvents 4

HCID 178418397HCID 178418397, compoundCatalystHCID 241BenzeneSolventHCID 702EthanolSolventHCID 962WaterSolvent2×

Procedure

2.10 g (7.50 mmol) of 2-fluoro-6-octyloxypyridine-3-boronic acid (prepared as described in Example 5) in 35 ml of ethanol are refluxed together with 2.70 g (7.50 mmol) of 4-bromo-4'-octyloxybiphenyl and 0.29 g (0.24 mmol) of tetrakis(triphenylphosphine)palladium in 46 ml of benzene and 2.5 g (23.40 mmol) of sodium carbonate in 11 ml of water for 20 hours. After distributing the reaction mixture between water and dichloromethane, the organic phase is washed with sodium chloride solution, dried over sodium sulfate, filtered and concentrated. Purification of the residue by chromatography (silica gel, dichloromethane) and recrystallization from acetonitrile give 0.50 g of 2-fluoro-6-octyloxy-3-[4-(4-octyloxyphenyl)phenyl]pyridine. ##STR32##

Workup

  1. washthe organic phase is washed with sodium chloride solution
  2. dry with materialdried over sodium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated
  5. customPurification of the residue
  6. customby chromatography (silica gel, dichloromethane) and recrystallization from acetonitrile

Sources & evidence

ORD record
ord-51874d2e1e3549caa257c4049dcb364b
Source dataset
uspto-grants-1997_05
Patent number
US05630962

Linked notes

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