Piperidine → n-{5-[5-(4-Chloro-phenyl)-pyridin-2-ylethynyl]-3-methyl-pyridin-2-yl}-2-pyrrolidin-1-yl-acetamide

HRID 1916744Notes

Reaction equation

HRID 1916744 reaction equation
[C:1]([C:3]1[CH:4]=[C:5]([CH3:18])[C:6]([NH:9][C:10](=[O:17])[CH2:11][N:12]2[CH2:16][CH2:15][CH2:14][CH2:13]2)=[N:7][CH:8]=1)#[CH:2].[Cl:19][C:20]1[CH:25]=[CH:24][C:23]([C:26]2[CH:27]=[CH:28][C:29](I)=[N:30][CH:31]=2)=[CH:22][CH:21]=1.N1CCCCC1>C1COCC1.Cl[Pd](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1.[Cu]I>[Cl:19][C:20]1[CH:21]=[CH:22][C:23]([C:26]2[CH:27]=[CH:28][C:29]([C:2]#[C:1][C:3]3[CH:4]=[C:5]([CH3:18])[C:6]([NH:9][C:10](=[O:17])[CH2:11][N:12]4[CH2:16][CH2:15][CH2:14][CH2:13]4)=[N:7][CH:8]=3)=[N:30][CH:31]=2)=[CH:24][CH:25]=1

Participants

7

Reactant 3

HCID 8082PiperidineHCID 85969661N-(5-ethynyl-3-methyl-pyridin-2-yl)-2-pyrrolidin-1-yl-acetamideHCID 859698495-(4-Chlorophenyl)-2-iodopyridine

Product 1

HCID 59835753n-{5-[5-(4-Chloro-phenyl)-pyridin-2-ylethynyl]-3-methyl-pyridin-2-yl}-2-pyrrolidin-1-yl-acetamide

Reagents, catalysts & solvents 3

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 178418476HCID 178418476, compoundCatalystHCID 8028TetrahydrofuranSolvent

Procedure

Under an argon atmosphere 4 mg (0.01 mmol) Pd(PPh3)2Cl2 and 1 mg (0.01 mmol) CuI are added to a solution of 73 mg (0.3 mmol) N-(5-ethynyl-3-methyl-pyridin-2-yl)-2-pyrrolidin-1-yl-acetamide and 95 mg (0.3 mmol) 5-(4-chloro-phenyl)-2-iodo-pyridine in 59 μL (0.6 mmol) piperidine and 10 mL THF and the reaction mixture is stirred for 30 min at RT. It is evaporated down i.vac., the residue is taken up in EtOAc, the organic phase is washed with water and saturated NaCl solution and dried over Na2SO4. After the desiccant and solvent have been eliminated the residue is purified first by chromatography (silica gel, EtOAc/MeOH/NH3 95:5:0.5) and then by HPLC.

Workup

  1. customIt is evaporated down i.vac
  2. washthe organic phase is washed with water and saturated NaCl solution
  3. dry with materialdried over Na2SO4
  4. customis purified first by chromatography (silica gel, EtOAc/MeOH/NH3 95:5:0.5)

Sources & evidence

ORD record
ord-882ca5315ec14cd580d2a040b081342f
Source dataset
uspto-grants-2013_12
Patent number
US08618132B2

Reaction notes

Loading…