Triethylamine → HCID 70656829, compound

HRID 1504116Notes

Reaction equation

HRID 1504116 reaction equation
[CH2:1]([N:3]1[C:9](=[O:10])[C:8]([CH3:12])([CH3:11])[C:7](=[O:13])[N:6]([CH3:14])[C:5]2[CH:15]=[C:16](OS(C(F)(F)F)(=O)=O)[CH:17]=[CH:18][C:4]1=2)[CH3:2].[CH2:27]([N:31]1[C:39](=[O:40])[C:38]2[C:33](=[CH:34][CH:35]=[CH:36][CH:37]=2)[C:32]1=[O:41])[CH2:28][C:29]#[CH:30].C(N(CC)CC)C>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.CN(C=O)C>[O:41]=[C:32]1[C:33]2[C:38](=[CH:37][CH:36]=[CH:35][CH:34]=2)[C:39](=[O:40])[N:31]1[CH2:27][CH2:28][C:29]#[C:30][C:16]1[CH:17]=[CH:18][C:4]2[N:3]([CH2:1][CH3:2])[C:9](=[O:10])[C:8]([CH3:12])([CH3:11])[C:7](=[O:13])[N:6]([CH3:14])[C:5]=2[CH:15]=1

Participants

7

Reactant 3

HCID 8471TriethylamineHCID 11171619N-(3-Butynyl)phthalimideHCID 86670475Trifluoromethanesulfonic acid 1-ethyl-3,3,5-trimethyl-2,4-dioxo-2,3,4,5-tetrahydro-1H-benzo[b][1,4]diazepine-7-yl ester

Product 1

HCID 70656829HCID 70656829, compoundYield 76.9%

Reagents, catalysts & solvents 3

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 178418476HCID 178418476, compoundCatalystHCID 6228DimethylformamideSolvent

Conditions

Temperature
150 °C

Procedure

Trifluoromethane sulfonic acid 1-ethyl-3,3,5-trimethyl-2,4-dioxo-2,3,4,5-tetrahydro-1H-benzo[b][1,4]diazepine-7-yl ester(0.59 g), 2-(but-3-ynyl)isoindol-1,3-dione(0.3 g), dichlorobis(triphenyl phosphine)palladium (II) (53 mg), copper(I) iodide(29 mg), and triethylamine(0.39 ml) were added to DMF(4 ml). The mixture was heated at 150° C. (microwave reactor) for 10 minutes. The reaction liquid was cooled to room temperature, and subjected to celite filtration. The filtrate was condensed under reduced pressure and the residue was purified by silica gel column chromatography (hexane: ethyl acetate=60:40→30:70). The purified product was condensed under reduced pressure to give the title compound(0.51 g) as a yellowish-white solid.

Workup

  1. customThe reaction liquid
  2. temperaturewas cooled to room temperature
  3. filtrationsubjected to celite filtration
  4. customcondensed under reduced pressure
  5. customthe residue was purified by silica gel column chromatography (hexane: ethyl acetate=60:40→30:70)
  6. customcondensed under reduced pressure

Sources & evidence

ORD record
ord-38068d3bd5eb4fb5bf4e4306699df962
Source dataset
uspto-grants-2015_12
Patent number
US09212187B2

Reaction notes

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