Ethanol → HCID 19387558, compound

HRID 1757362Notes

Reaction equation

HRID 1757362 reaction equation
Br[C:2]1[CH:3]=[C:4]([F:23])[C:5]([C:8]2[CH:13]=[CH:12][C:11]([O:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH3:22])=[CH:10][CH:9]=2)=[N:6][CH:7]=1.[CH2:24]([O:32][C:33]1[CH:38]=[CH:37][C:36](B(O)O)=[CH:35][CH: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>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>[F:23][C:4]1[C:5]([C:8]2[CH:13]=[CH:12][C:11]([O:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH3:22])=[CH:10][CH:9]=2)=[N:6][CH:7]=[C:2]([C:36]2[CH:37]=[CH:38][C:33]([O:32][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH3:31])=[CH:34][CH:35]=2)[CH:3]=1

Participants

8

Reactant 4

HCID 702EthanolHCID 10340Sodium CarbonateHCID 39772844-n-Octyloxyphenylboronic Acid (contains varying amounts of Anhydride)HCID 193875465-Bromo-3-fluoro-2-(4-octyloxyphenyl)pyridine

Product 1

HCID 19387558HCID 19387558, compoundYield 70%

Reagents, catalysts & solvents 3

HCID 178418397HCID 178418397, compoundCatalystHCID 962WaterSolventHCID 1140TolueneSolvent

Procedure

4.00 g (10.51 mmol) of 5-bromo-3-fluoro-2-(4-octyloxyphenyl)pyridine, 2.63 g (10.51 mmol) of 4-octyloxybenzeneboronic acid, 0.12 g (0.11 mmol) of tetrakis(triphenylphosphine)palladium(0) and 2.23 g (21.02 mmol) of sodium carbonate are heated at 80° C. for 3 hours in 100 ml of toluene, 70 ml of ethanol and 40 ml of water. The mixture is subsequently partitioned between aqueous sodium chloride solution and ether, and the organic phase is washed with aqueous sodium chloride solution, dried over sodium sulfate, evaporated and purified by chromatography (silica gel/dichloromethane), giving 3.72 g of 3-fluoro-2,5-di(4-octyloxyphenyl)pyridine. ##STR26## The compound has the phase sequence: X 88 (77.9) Sc 142 SA 171 N 172 I.

Workup

  1. customThe mixture is subsequently partitioned between aqueous sodium chloride solution and ether
  2. washthe organic phase is washed with aqueous sodium chloride solution
  3. dry with materialdried over sodium sulfate
  4. customevaporated
  5. custompurified by chromatography (silica gel/dichloromethane)

Sources & evidence

ORD record
ord-59542e11cd6f481f8b5dc20c69e82937
Source dataset
uspto-grants-1995_08
Patent number
US05445763

Reaction notes

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