Dichloromethane → Tert-butyl 1-(4-((4-ethoxyphenyl)ethynyl)phenyl)propan-2-yl-carbamate

HRID 76168

Reaction equation

HRID 76168 reaction equation
[C:1]([O:5][C:6](=[O:18])[NH:7][CH:8]([CH3:17])[CH2:9][C:10]1[CH:15]=[CH:14][C:13](I)=[CH:12][CH:11]=1)([CH3:4])([CH3:3])[CH3:2].[CH2:19]([O:21][C:22]1[CH:27]=[CH:26][C:25]([C:28]#[CH:29])=[CH:24][CH:23]=1)[CH3:20].ClCCl>C(#N)C.[Cu]I>[C:1]([O:5][C:6](=[O:18])[NH:7][CH:8]([CH3:17])[CH2:9][C:10]1[CH:15]=[CH:14][C:13]([C:29]#[C:28][C:25]2[CH:26]=[CH:27][C:22]([O:21][CH2:19][CH3:20])=[CH:23][CH:24]=2)=[CH:12][CH:11]=1)([CH3:4])([CH3:3])[CH3:2]

Participants

6

Reactant 3

HCID 6344DichloromethaneHCID 27751241-Ethoxy-4-ethynylbenzeneHCID 15576539[2-(4-Iodo-phenyl)-1-methyl-ethyl]-carbamic acid tert-butyl ester

Product 1

HCID 66611490Tert-butyl 1-(4-((4-ethoxyphenyl)ethynyl)phenyl)propan-2-yl-carbamate

Reagents, catalysts & solvents 2

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 6342AcetonitrileSolvent

Procedure

To 5.00 g (13.8 mmol) [2-(4-iodo-phenyl)-1-methyl-ethyl]-carbamic acid tert-butyl ester (I52.5) and 2.02 g (13.8 mmol) 4-ethoxyphenylacetylene in 80 mL ACN are added 4.46 mL (32.2 mmol) TEA, 135.6 mg (0.17 mmol) [1,1′-bis(diphenyl-phosphino)ferrocene]dichloropalladium(II) complex with dichloromethane and 32.3 mg (0.17 mmol) CuI, and the reaction mixture is stirred at r.t. over night. The precipitate is filtered and washed with ACN. The resulting crude product is purified by column chromatography (CyH/EtOAc 100/0→90/10).

Workup

  1. filtrationThe precipitate is filtered
  2. washwashed with ACN
  3. customThe resulting crude product is purified by column chromatography (CyH/EtOAc 100/0→90/10)

Sources & evidence

ORD record
ord-267c18524a75466daf6e51e2fb4d4337
Source dataset
uspto-grants-2014_09
Patent number
US08835472B2

Linked notes

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