Cesium carbonate → 5-(4-Chloro-phenyl)-2-[3-(4-pyrrolidin-1-ylmethyl-phenyl)-prop-2-ynyloxy]-pyridine

HRID 1916728Notes

Reaction equation

HRID 1916728 reaction equation
C([O-])([O-])=O.[Cs+].[Cs+].[Cl:7][C:8]1[CH:13]=[CH:12][C:11]([C:14]2[CH:15]=[CH:16][C:17]([O:20][CH2:21][C:22]#[CH:23])=[N:18][CH:19]=2)=[CH:10][CH:9]=1.I[C:25]1[CH:36]=[CH:35][C:28]([CH2:29][N:30]2[CH2:34][CH2:33][CH2:32][CH2:31]2)=[CH:27][CH:26]=1>C1COCC1.[Cu]I>[Cl:7][C:8]1[CH:13]=[CH:12][C:11]([C:14]2[CH:15]=[CH:16][C:17]([O:20][CH2:21][C:22]#[C:23][C:25]3[CH:26]=[CH:27][C:28]([CH2:29][N:30]4[CH2:34][CH2:33][CH2:32][CH2:31]4)=[CH:35][CH:36]=3)=[N:18][CH:19]=2)=[CH:10][CH:9]=1

Participants

6

Reactant 3

HCID 10796Cesium carbonateHCID 185258671-(4-Iodobenzyl)pyrrolidineHCID 859696065-(4-Chloro-phenyl)-2-prop-2-ynyloxy-pyridine

Product 1

HCID 598357275-(4-Chloro-phenyl)-2-[3-(4-pyrrolidin-1-ylmethyl-phenyl)-prop-2-ynyloxy]-pyridine

Reagents, catalysts & solvents 2

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 8028TetrahydrofuranSolvent

Procedure

Under an N2 atmosphere 221 mg (0.68 mmol) Cs2CO3, 4 mg (0.02 mmol) CuI and 23 mg (0.02 mmol) tetrakis-triphenylphosphane-palladium are added to a solution of 110 mg (0.45 mmol) 5-(4-chloro-phenyl)-2-prop-2-ynyloxy-pyridine and 129 mg (0.45 mmol) 1-(4-iodo-benzyl)-pyrrolidine in 9 mL THF and the reaction mixture is stirred for 4.5 h at RT. The mixture is evaporated down i. vac., the residue is combined with 20 mL 3% NH3 solution and 40 mL EtOAc, the organic phase is separated off and dried over Na2SO4. After the desiccant and solvent have been eliminated the residue is purified first by HPLC and then by chromatography (silica gel, DCM/MeOH/NH3 19:1:0.1).

Workup

  1. customThe mixture is evaporated down i
  2. customthe organic phase is separated off
  3. dry with materialdried over Na2SO4
  4. customis purified first by HPLC

Sources & evidence

ORD record
ord-7f244b21bd784ce089b91846959549f6
Source dataset
uspto-grants-2013_12
Patent number
US08618132B2

Reaction notes

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