Sodium Sulfate → 2-Fluoro-3-(5-octyl-1,3-dioxaborinan-2-yl)-6-(4-octyloxyphenyl)pyridine

HRID 1780570Notes

Reaction equation

HRID 1780570 reaction equation
[F:1][C:2]1[C:7]([B:8]([OH:10])[OH:9])=[CH:6][CH:5]=[C:4]([C:11]2[CH:16]=[CH:15][C:14]([O:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH3:25])=[CH:13][CH:12]=2)[N:3]=1.[CH2:26]([CH:34]([CH2:37]O)[CH2:35]O)[CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH3:33].S([O-])([O-])(=O)=O.[Na+].[Na+]>O1CCCC1>[F:1][C:2]1[C:7]([B:8]2[O:9][CH2:35][CH:34]([CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH3:33])[CH2:37][O:10]2)=[CH:6][CH:5]=[C:4]([C:11]2[CH:16]=[CH:15][C:14]([O:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH3:25])=[CH:13][CH:12]=2)[N:3]=1

Participants

5

Reactant 3

HCID 24436Sodium SulfateHCID 3160622-Octylpropane-1,3-diolHCID 190469502-Fluoro-6-(4-octyloxyphenyl)pyridine-3-boronic acid

Product 1

HCID 676045522-Fluoro-3-(5-octyl-1,3-dioxaborinan-2-yl)-6-(4-octyloxyphenyl)pyridineYield 83.1%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

1.00 g (3.00 mmol) of 2-fluoro-6-(4-octyloxyphenyl)pyridine-3-boronic acid (prepared as described in Example 10), 0.56 g (3.00 mmol) of 2-octylpropane-1,3-diol and 1.50 g of sodium sulfate in 30 ml of tetrahydrofuran are stirred at room temperature for 48 hours. Sodium sulfate is then filtered off, the filtrate is concentrated, and the residue is recrystallized from hexane, giving 1.24 g of 2-fluoro-3-(5-octyl-1,3-dioxaborinan-2-yl)-6-(4-octyloxyphenyl)pyridine. ##STR61##

Workup

  1. filtrationSodium sulfate is then filtered off
  2. concentrationthe filtrate is concentrated
  3. customthe residue is recrystallized from hexane

Sources & evidence

ORD record
ord-cf26755b29dd4b6aa8073ddb8532d255
Source dataset
uspto-grants-1997_05
Patent number
US05630962

Reaction notes

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