4-Ethynylaniline → 4-(4-aminophenylethynyl)-2,6-bis(N,N-bis(t-butoxycarbonylmethyl)aminomethyl)pyridine

HRID 2073919Notes

Reaction equation

HRID 2073919 reaction equation
I[C:2]1[CH:7]=[C:6]([CH2:8][N:9]([CH2:18][C:19]([O:21][C:22]([CH3:25])([CH3:24])[CH3:23])=[O:20])[CH2:10][C:11]([O:13][C:14]([CH3:17])([CH3:16])[CH3:15])=[O:12])[N:5]=[C:4]([CH2:26][N:27]([CH2:36][C:37]([O:39][C:40]([CH3:43])([CH3:42])[CH3:41])=[O:38])[CH2:28][C:29]([O:31][C:32]([CH3:35])([CH3:34])[CH3:33])=[O:30])[CH:3]=1.[NH2:44][C:45]1[CH:50]=[CH:49][C:48]([C:51]#[CH:52])=[CH:47][CH:46]=1>C(N(CC)CC)C.C(Cl)(Cl)Cl.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>[NH2:44][C:45]1[CH:50]=[CH:49][C:48]([C:51]#[C:52][C:2]2[CH:3]=[C:4]([CH2:26][N:27]([CH2:36][C:37]([O:39][C:40]([CH3:42])([CH3:41])[CH3:43])=[O:38])[CH2:28][C:29]([O:31][C:32]([CH3:34])([CH3:35])[CH3:33])=[O:30])[N:5]=[C:6]([CH2:8][N:9]([CH2:10][C:11]([O:13][C:14]([CH3:16])([CH3:17])[CH3:15])=[O:12])[CH2:18][C:19]([O:21][C:22]([CH3:24])([CH3:25])[CH3:23])=[O:20])[CH:7]=2)=[CH:47][CH:46]=1

Participants

7

Reactant 2

HCID 37600254-EthynylanilineHCID 141457414iodo-2,6-bis(N,N-bis(t-butoxycarbonylmethyl)aminomethyl)pyridine

Product 1

HCID 542122224-(4-aminophenylethynyl)-2,6-bis(N,N-bis(t-butoxycarbonylmethyl)aminomethyl)pyridine

Reagents, catalysts & solvents 4

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 178418476HCID 178418476, compoundCatalystHCID 6212ChloroformSolventHCID 8471TriethylamineSolvent

Procedure

A mixture of compound 1 (1.08 g, 1.5 mmol), bis(triphenylphosphine)palladium(II) chloride (21 mg, 0.03 mmol), copper(I) iodide (11 mg, 0.06 mmol) and p-aminophenylacetylene (176 mg, 1.5 mmol) in 10 mL of triethylamine was deaerated with nitrogen and kept at 40° C. for 1.5 h. The mixture was diluted with 40 mL of chloroform, washed with water and dried with sodium sulfate. The solution was evaporated in vacuo and the product was obtained as a yellow oil.

Workup

  1. washwashed with water
  2. dry with materialdried with sodium sulfate
  3. customThe solution was evaporated in vacuo
  4. customthe product was obtained as a yellow oil

Sources & evidence

ORD record
ord-3ddc72825ded42dd94c5b717726feffc
Source dataset
uspto-grants-1990_04
Patent number
US04920195

Reaction notes

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