Sodium Carbonate → 5-(4-Chloro-phenyl)-2-[4-(2-pyrrolidin-1-yl-ethoxy)-phenylethynyl]-pyridine

HRID 1916524Notes

Reaction equation

HRID 1916524 reaction equation
Br[C:2]1[CH:3]=[CH:4][C:5]([C:8]#[C:9][C:10]2[CH:15]=[CH:14][C:13]([O:16][CH2:17][CH2:18][N:19]3[CH2:23][CH2:22][CH2:21][CH2:20]3)=[CH:12][CH:11]=2)=[N:6][CH:7]=1.[Cl:24][C:25]1[CH:30]=[CH:29][C:28](OB(O)O)=[CH:27][CH:26]=1.C([O-])([O-])=O.[Na+].[Na+]>O1CCOCC1>[Cl:24][C:25]1[CH:30]=[CH:29][C:28]([C:2]2[CH:3]=[CH:4][C:5]([C:8]#[C:9][C:10]3[CH:15]=[CH:14][C:13]([O:16][CH2:17][CH2:18][N:19]4[CH2:23][CH2:22][CH2:21][CH2:20]4)=[CH:12][CH:11]=3)=[N:6][CH:7]=2)=[CH:27][CH:26]=1

Participants

5

Reactant 3

HCID 10340Sodium CarbonateHCID 17810664p-Chlorophenylboric acidHCID 673653025-Bromo-2-[4-(2-pyrrolidin-1-yl-ethoxy)-phenylethynyl]-pyridine

Product 1

HCID 99784905-(4-Chloro-phenyl)-2-[4-(2-pyrrolidin-1-yl-ethoxy)-phenylethynyl]-pyridine

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Conditions

Temperature
100 °C

Procedure

A mixture of 2.97 g (8.0 mmol) 5-bromo-2-[4-(2-pyrrolidin-1-yl-ethoxy)-phenylethynyl]-pyridine, 2.50 g (16.0 mmol) 4-chloro-phenylboric acid, 462 mg (0.4 mmol) tetrakis-triphenylphosphane-palladium and 8.0 mL of a 2M aqueous Na2CO3 solution in 100 mL 1,4-dioxane is heated for 4 h at 100° C. under an argon atmosphere. The solvent is distilled off i.vac., the residue is stirred with water/EtOAc (1/1, v/v), suction filtered through a fibreglass filter, the organic phase is washed with saturated, aqueous NaCl solution and dried over Na2SO4. After the desiccant and solvent have been eliminated the residue is purified by chromatography (Alox, cyc/EtOAc 2:1). The product fractions are evaporated down, the residue is triturated with diethyl ether, suction filtered and washed with diethyl ether.

Workup

  1. distillationThe solvent is distilled off i.vac
  2. filtrationv/v), suction filtered through a fibreglass
  3. filtrationfilter
  4. washthe organic phase is washed with saturated, aqueous NaCl solution
  5. dry with materialdried over Na2SO4
  6. customis purified by chromatography (Alox, cyc/EtOAc 2:1)
  7. customThe product fractions are evaporated down
  8. customthe residue is triturated with diethyl ether, suction
  9. filtrationfiltered
  10. washwashed with diethyl ether

Sources & evidence

ORD record
ord-6e78ca90f9914582959e292e8a4c16a2
Source dataset
uspto-grants-2013_12
Patent number
US08618132B2

Reaction notes

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