4-Fluoroiodobenzene → 3-(4-Fluoro-phenylethynyl)-piperidine-1-carboxylic acid tert-butyl ester

HRID 1661168Notes

Reaction equation

HRID 1661168 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][CH2:11][CH:10]([C:14]#[CH:15])[CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].I[C:17]1[CH:22]=[CH:21][C:20]([F:23])=[CH:19][CH:18]=1>CCN(CC)CC.[Cu]I.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>[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][CH2:11][CH:10]([C:14]#[C:15][C:17]2[CH:22]=[CH:21][C:20]([F:23])=[CH:19][CH:18]=2)[CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2]

Participants

6

Reactant 2

HCID 96054-FluoroiodobenzeneHCID 21963855tert-Butyl 3-ethynylpiperidine-1-carboxylate

Product 1

HCID 666186503-(4-Fluoro-phenylethynyl)-piperidine-1-carboxylic acid tert-butyl esterYield 89%

Reagents, catalysts & solvents 3

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 178418476HCID 178418476, compoundCatalystHCID 8471TriethylamineSolvent

Conditions

Temperature
60 °C

Procedure

To a suspension of CuI (4 mg, 0.02 mmol) in Et3N (1 ml) was added 3-Ethynyl-piperidine-1-carboxylic acid tert-butyl ester (80 mg, 0.38 mmol) followed by PdCl2(PPh3)2 (13 mg, 0.02 mmol) and 1-Iodo-4-fluoro-benzene (85 mg, 0.38 mmol). The mixture was stirred 1 h at R.T then heated to 60° C. for 12 h. Et3N was removed by evaporation. The product was purified by flash chromatography (DCM 100%) to give 0.1 g (89%) of 3-(4-Fluoro-phenylethynyl)-piperidine-1-carboxylic acid tert-butyl ester as a yellow oil.

Workup

  1. customEt3N was removed by evaporation
  2. customThe product was purified by flash chromatography (DCM 100%)

Sources & evidence

ORD record
ord-5c96f47e0df44f5fb5af208b5ab7f8f9
Source dataset
uspto-grants-2011_10
Patent number
US08030331B2

Reaction notes

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