Ethyl Acetate → Tert-butyl 2-(4-((4-propoxyphenyl)ethynyl)phenyl)propyl-carbamate

HRID 76169Notes

Reaction equation

HRID 76169 reaction equation
[C:1]([O:5][C:6](=[O:18])[NH:7][CH2:8][CH:9]([C:11]1[CH:16]=[CH:15][C:14](I)=[CH:13][CH:12]=1)[CH3:10])([CH3:4])([CH3:3])[CH3:2].[C:19]([C:21]1[CH:26]=[CH:25][C:24]([O:27][CH2:28][CH2:29][CH3:30])=[CH:23][CH:22]=1)#[CH:20].CCN(C(C)C)C(C)C.CCOC(C)=O>C1COCC1.[Cu]I>[C:1]([O:5][C:6](=[O:18])[NH:7][CH2:8][CH:9]([C:11]1[CH:16]=[CH:15][C:14]([C:20]#[C:19][C:21]2[CH:26]=[CH:25][C:24]([O:27][CH2:28][CH2:29][CH3:30])=[CH:23][CH:22]=2)=[CH:13][CH:12]=1)[CH3:10])([CH3:4])([CH3:3])[CH3:2]

Participants

7

Reactant 4

HCID 8857Ethyl AcetateHCID 81531DiisopropylethylamineHCID 27751231-Ethynyl-4-propoxybenzeneHCID 66611182[2-(4-Iodo-phenyl)-propyl]-carbamic acid tert-butyl ester

Product 1

HCID 66612060Tert-butyl 2-(4-((4-propoxyphenyl)ethynyl)phenyl)propyl-carbamate

Reagents, catalysts & solvents 2

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

Procedure

To 1.00 g (2.77 mmol) [2-(4-iodo-phenyl)-propyl]-carbamic acid tert-butyl ester (152.8) and 0.44 g (2.77 mmol) 1-ethinyl-4-propoxybenzene in 25 mL THF are added 0.78 mL (5.54 mmol) DIPEA, 40.5 mg (0.06 mmol) [1,1′-bis(diphenyl-phosphino)ferrocene]dichloropalladium(II) and 10.6 mg (0.055 mmol) CuI. The reaction mixture is stirred at r.t. for 3 h. EtOAc is added and the mixture is washed with diluted aq. ammonia solution (1×) and water (1×), dried with MgSO4 and the solvent is removed in vacuo. The crude product is purified by column chromatography (silica gel, PE/EtOAc 9/1).

Workup

  1. washthe mixture is washed with diluted aq. ammonia solution (1×) and water (1×)
  2. dry with materialdried with MgSO4
  3. customthe solvent is removed in vacuo
  4. customThe crude product is purified by column chromatography (silica gel, PE/EtOAc 9/1)

Sources & evidence

ORD record
ord-3b920fd56c974cf8927834feaffc498b
Source dataset
uspto-grants-2014_09
Patent number
US08835472B2

Reaction notes

Loading…