Piperidine → 2-{4-[5-(4-Chlorophenyl)pyrazin-2-ylethynyl]phenoxy}ethanol

HRID 734881Notes

Reaction equation

HRID 734881 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:13]=[N:12][C:11](I)=[CH:10][N:9]=2)=[CH:4][CH:3]=1.[C:15]([C:17]1[CH:26]=[CH:25][C:20]([O:21][CH2:22][CH2:23][OH:24])=[CH:19][CH:18]=1)#[CH:16].N1CCCCC1>C1COCC1.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.Cl[Pd]Cl.[Fe+2].[Cu]I>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[N:9]=[CH:10][C:11]([C:16]#[C:15][C:17]3[CH:26]=[CH:25][C:20]([O:21][CH2:22][CH2:23][OH:24])=[CH:19][CH:18]=3)=[N:12][CH:13]=2)=[CH:4][CH:3]=1

Participants

7

Reactant 3

HCID 8082PiperidineHCID 187514152-(4-Ethynylphenoxy)ethan-1-olHCID 859696362-(4-Chlorophenyl)-5-iodopyrazine

Product 1

HCID 690588142-{4-[5-(4-Chlorophenyl)pyrazin-2-ylethynyl]phenoxy}ethanol

Reagents, catalysts & solvents 3

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 178418228Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)CatalystHCID 8028TetrahydrofuranSolvent

Procedure

Under an argon atmosphere 49 mg (0.06 mmol) of PdCl2(dppf) and 11 mg (0.06 mmol) of CuI were added to a repeatedly degassed solution of 535 mg (3.30 mmol) of 2-(4-chlorophenyl)-5-iodopyrazine, 950 mg (3.30 mmol) of 2-(4-ethynylphenoxy)ethanol, and 0.59 mL (6.00 mmol) of piperidine in 50 mL of THF and the mixture was stirred for 4 hours at RT. The precipitate was suction filtered and washed with acetonitrile. The mother liquor was concentrated, and the precipitate formed was filtered off and washed with acetonitrile. The precipitates were combined. Yield: 700 mg (67% of theoretical); C20H15ClN2O2 (M=350.798); calc.: molpeak (M+H)+:351/353 (Cl); found: molpeak (M+H)+:351/353 (Cl); Rf value: 0.30 (silica gel, PE/EtOAc 1:1).

Workup

  1. filtrationfiltered
  2. washwashed with acetonitrile
  3. concentrationThe mother liquor was concentrated
  4. customthe precipitate formed
  5. filtrationwas filtered off
  6. washwashed with acetonitrile

Sources & evidence

ORD record
ord-ac501f2c3d544056a1bc86978d6f5c22
Source dataset
uspto-grants-2009_09
Patent number
US07592358B2

Reaction notes

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