Diisopropylamine → HCID 10378725, compound

HRID 915508Notes

Reaction equation

HRID 915508 reaction equation
C(P(C(C)(C)C)C(C)(C)C)(C)(C)C.[CH:14]([NH:17][CH:18]([CH3:20])C)(C)C.Br[C:22]1[CH:27]=[C:26]([C:28]#[N:29])[CH:25]=[CH:24][C:23]=1[O:30][C:31](=O)[CH3:32].[C:34]1(C#C)C=[CH:38][CH:37]=[CH:36][CH:35]=1.C(OCC)(=[O:44])C>[Cu]I.C1C=CC(C#N)=CC=1.C1C=CC(C#N)=CC=1.Cl[Pd]Cl.O1CCOCC1>[CH3:14][NH:17][C:18]([C:20]1[C:22]2[CH:27]=[C:26]([C:28]#[N:29])[CH:25]=[CH:24][C:23]=2[O:30][C:31]=1[C:32]1[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=1)=[O:44]

Participants

9

Reactant 5

HCID 7912DiisopropylamineHCID 8857Ethyl AcetateHCID 10821PhenylacetyleneHCID 83681Tris(1,1-dimethylethyl)phosphineHCID 12709354HCID 12709354, compound

Product 1

HCID 10378725HCID 10378725, compoundYield 72%

Reagents, catalysts & solvents 3

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 498840Bis(benzonitrile)palladium chlorideCatalystHCID 312751,4-DioxaneSolvent

Procedure

Preparation of compound 26(a) (acetic acid 4-cyano-2-phenylethynyl-phenyl ester). 1,4-Dioxane (2.5 mL, dry) was added to a stirred suspension of CuI (8.0 mg, 2 mol %) and dichlorobis(benzonitrile)palladium (II) (24 mg, 3 mol %) in a dry septum-capped flask with constant purging of argon. Tri-t-butylphosphine (542 μl, 0.25M solution in 1,4-dioxane), diisopropyl amine (350 μl, 4.17 mmol), acetic acid 2-bromo-4-cyano-phenyl ester (500 mg, 2.08 mmol), and phenyl acetylene (254 mg, 2.71 mmol) were added with syringes to the stirred reaction mixture. The reaction mixture was stirred for 6 hours, and then diluted with ethyl acetate and passed through small pad of silica gel. The filtrate was concentrated, and the crude product was purified by column chromatography (silica gel, 5 to 20% ethyl acetate in hexanes) to provide 390 mg (72%) of the desired product.

Workup

  1. customseptum-capped flask
  2. customwith constant purging of argon
  3. concentrationThe filtrate was concentrated
  4. customthe crude product was purified by column chromatography (silica gel, 5 to 20% ethyl acetate in hexanes)

Sources & evidence

ORD record
ord-0c5786250d0341c49bc6f32105eae95b
Source dataset
uspto-grants-2007_09
Patent number
US07265152B2

Reaction notes

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