Water → HCID 67363953, compound

HRID 1916692Notes

Reaction equation

HRID 1916692 reaction equation
I[C:2]1[CH:11]=[CH:10][C:5]([O:6][CH2:7][CH2:8][OH:9])=[CH:4][CH:3]=1.[Cl:12][C:13]1[CH:18]=[CH:17][C:16]([C:19]2[CH:20]=[CH:21][C:22]([C:25]#[CH:26])=[N:23][CH:24]=2)=[CH:15][CH:14]=1.O.CCOC(C)=O>N1CCCCC1.[Cu]I>[Cl:12][C:13]1[CH:14]=[CH:15][C:16]([C:19]2[CH:20]=[CH:21][C:22]([C:25]#[C:26][C:2]3[CH:11]=[CH:10][C:5]([O:6][CH2:7][CH2:8][OH:9])=[CH:4][CH:3]=3)=[N:23][CH:24]=2)=[CH:17][CH:18]=1

Participants

7

Reactant 4

HCID 962WaterHCID 8857Ethyl AcetateHCID 35132082-(4-Iodophenoxy)ethanolHCID 578453285-(4-Chloro-phenyl)-2-ethynyl-pyridine

Product 1

HCID 67363953HCID 67363953, compound

Reagents, catalysts & solvents 2

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 8082PiperidineSolvent

Procedure

Under an argon atmosphere 253 mg (0.22 mmol) tetrakis-triphenylphosphane-palladium and 42 mg (0.22 mmol) CuI are added to a solution of 2.9 g (11 mmol) 2-(4-iodo-phenoxy)-ethanol and 2.35 g (11 mmol) 5-(4-chloro-phenyl)-2-ethynyl-pyridine in 50 mL piperidine and the reaction mixture is stirred for 30 min at RT. The solvent is eliminated i.vac., the residue is combined with water and stirred with EtOAc. The product precipitated is suction filtered and dried.

Workup

  1. customThe product precipitated
  2. filtrationfiltered
  3. customdried

Sources & evidence

ORD record
ord-45fe597784e64715ae44abf0a7de67b6
Source dataset
uspto-grants-2013_12
Patent number
US08618132B2

Reaction notes

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