Piperidine → Ethyl 2-((2-(tert-butoxycarbonyl(3-(thiophen-2-yl)prop-2-ynyl)amino)ethyl)-(isopropyl)amino)-2-oxoacetate

HRID 1971677Notes

Reaction equation

HRID 1971677 reaction equation
[C:1]([O:5][C:6]([N:8]([CH2:22][C:23]#[CH:24])[CH2:9][CH2:10][N:11]([CH:19]([CH3:21])[CH3:20])[C:12](=[O:18])[C:13]([O:15][CH2:16][CH3:17])=[O:14])=[O:7])([CH3:4])([CH3:3])[CH3:2].I[C:26]1[S:27][CH:28]=[CH:29][CH:30]=1.N1CCCCC1>C1(C)C=CC=CC=1.[Cu]I>[C:1]([O:5][C:6]([N:8]([CH2:22][C:23]#[C:24][C:26]1[S:27][CH:28]=[CH:29][CH:30]=1)[CH2:9][CH2:10][N:11]([CH:19]([CH3:21])[CH3:20])[C:12](=[O:18])[C:13]([O:15][CH2:16][CH3:17])=[O:14])=[O:7])([CH3:2])([CH3:3])[CH3:4]

Participants

6

Reactant 3

HCID 8082PiperidineHCID 189212-IodothiopheneHCID 58124862Ethyl 2-((2-(tert-butoxycarbonyl(prop-2-ynyl)amino)ethyl)(isopropyl)amino)-2-oxoacetate

Product 1

HCID 58124877Ethyl 2-((2-(tert-butoxycarbonyl(3-(thiophen-2-yl)prop-2-ynyl)amino)ethyl)-(isopropyl)amino)-2-oxoacetate

Reagents, catalysts & solvents 2

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 1140TolueneSolvent

Procedure

A solution of 340 mg of 10g, 130 μl of 2-iodothiophene, 12 mg of CuI, 21 mg of PdCl2(PPh4)2 and 200 μl of piperidine in 2 ml of degassed toluene was stirred under N2 for 3 h. The mixture was concentrated and applied to a silica column and chromatographed with a gradient of heptane/ethyl acetate, to provide 400 mg of 10h as an orange oil. Rf 0.60 (hept/ethyl acetate 1/1).

Workup

  1. concentrationThe mixture was concentrated
  2. customchromatographed with a gradient of heptane/ethyl acetate

Sources & evidence

ORD record
ord-2f9ddaa69383445188c028715bee33b4
Source dataset
uspto-grants-2013_04
Patent number
US08431564B2

Reaction notes

Loading…